


Feathers and Pitchforks

by TobytheWise



Category: Supernatural
Genre: Alternate Universe, Angel Castiel (Supernatural), Angst, Angst with a Happy Ending, Bottom Castiel, Canon-Typical Violence, Demon Deals, Demon Dean Winchester, Demon Sam Winchester, Drinking, Enemies to Lovers, Explicit Language, Grace Kink, Grace Sex, Humor, Hurt/Comfort, Implied Switching, Implied/Referenced Drug Use, M/M, Minor Dorothy Baum/Charlie Bradbury, Minor Garth/Bess, Minor Jack/Clark, Petty Competitions, Pranks and Practical Jokes, Romantic Comedy, Serious Injuries, Soulless Charlie, Top Dean Winchester, True Love's Kiss, Wing Kink, sorta - Freeform, the Angel and Demon on your shoulder
Language: English
Status: Completed
Published: 2018-10-10
Updated: 2018-10-10
Packaged: 2019-07-28 19:26:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 20,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16248269
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: On their eighteenth birthday, every person is assigned two guardians to help them make the best choices in life, ‘the angel and demon on their shoulder’.For hundred of years, Dean, a demon, and Castiel, an angel, have been forced to work together - helping their charges through the ups and downs of life. Instead of a blooming friendship, their partnership begins entirely on the wrong foot, causing tension and hatred towards each other. Lifetime after lifetime brings them bickering worse than any old married couple, arguing over the most obscene things, betting on who their charge will pick this time, and of course, obnoxious flirtations that make all of their charges either uncomfortable or roll their eyes.Despite not being allowed to pick favorites, their latest charge Charlie, wiggles her way into their hearts, right before making the worst decision of her life.Dean and Castiel will have to put their differences aside in order to save her, going above and beyond the call of duty. Will they be able to work together for the greater good, finding things out about themselves and each other along the way? Or will this mission end with cliche tragedy?





	Feathers and Pitchforks

**Author's Note:**

> This story is written for the DeanCas BigBang. Thanks to the mods for doing a wonderful job of running this amazing writing challenge!  
> Special thanks to my artist,[Horrorfemme](http://horrorfemme1138.tumblr.com/) who did an amazing job bringing this story to life with their beautiful works of art!!  
> Shoutout to my bestie, [LadyofThursday](https://ladyofthursday.tumblr.com/)! Thank you so much for encouraging me to sign up for the Big Bang this year and being my personal cheerleader. And thank you so so much for beta reading this for me! I couldn't have done this without you!

Dean takes another gulp of his beer, watching his little brother continue with his animated story. When Sammy has a drink or two in him, he begins using his hands wildly to convey the emotion of the story and it never fails to make Dean smile. 

“So get this: our last charge was deciding which major she should go into. She was split so of course Jo and I show up to help weigh the pros and cons. She was leaning towards starting nursing classes or criminal justice.” Sam takes a moment to take a swig of his own beer while shaking his head. “And you  _ know _ Jo is encouraging her to follow in her dad’s steps and go into criminal justice to become a cop.  _ But _ our girl has never wanted to actually do that! She’s always wanted to help people!”

“I think I see where this is going,” Dean says with a wince. 

“Jo and I get into an argument because of course she thinks everything can be solved with violence, therefore, this girl should become a cop so she can kick people’s asses. I remain calm and try to argue rationally. You’ll never guess what happens next.”

Dean mimics throwing something at his brother. “The knives come out?”

“The fucking knives come out!” Sam yells. “This poor girl is staring at us with wide, panicked eyes as Jo begins to literally throw knives at me!” Sam slumps down in the booth. “Why must she always argue with the knives, Dean? I’m the demon in this relationship but you’d never guess by our discussions. She’s always trying to lead our charges to the  _ fun _ choices. Studying for your test might be less fun than going to a party, but at least you’ll pass your exams.”

Sam’s rant seems to be over for the moment as he guzzles the rest of his beer down. 

“At least you guys get along all the other time you’re together. Your fights stay within the decision making arguments.”

Sam nods his head. “That’s true. I don’t know if I could handle being stationed with Jo if she acted like that all the time. The good thing about her is that once a decision has been made she sticks by our charge. That girl decided to become a nurse, rocking all her classes. And at least Jo always uses knives that don’t leave any lasting damage.” Sam finally smiles. “Plus the one time she accidently hit me and caused damage, she at least used her grace to help heal me.”

Dean begins making obscene gagging noise. “Get a room already.”

“Oh shut the fuck up, Dean.”

“All I’m saying, Sammy, is that your angel isn’t so bad.  _ My  _ angel on the other hand.”

Sam begins groaning, “seriously Dean? All you ever talk about is Cas this and Cas that. If I didn’t know any better I’d say you were in love with the guy.”

“Fat chance of that. I’d have to actually stand being in the same room with the guy for more than five seconds.”

Sam rolls his eyes and picks up the beer the waitress just dropped off. “All I’m saying is you have a lot to say about the guy who you claim to hate. Plus, you know what they say about schoolyard crushes. Maybe you’re both so mean to each other because you’re both secretly in love each other and don’t know how to express it.”

“Oh fuck you, Samantha. Sorry for trying to cheer you up with a story of my own.” Dean crosses his arms on his chest and sulks aggressively.

“Alright, Dean. Spill. What happened now?”

Dean smirks. “Well, little brother, this story is sure to top yours. So I went out and got myself a delicious apple pie, fresh from a bakery. You  _ know _ how I love my apple fucking pie.”

Sam winces. “What did he do?”

“I set it down so that I could use my mojo to shrink both myself and the pie since it was during the time we were with Balthazar. That asshole gave us a freakin’ shoe box to live in. So anyway, I shrink us both down and when I sit down to start eating I hear a chuckle from Cas. Cas chuckling is never a good thing. So I look down, ignoring Mr. Chucklehead and I find that my motherfucking pie has a motherfucking devil’s trap on it.”

Dean slumps down, seething at the memory of that poor, delicious pie. When he looks back up, Sam’s face is deep red and he’s desperately trying not to laugh out loud. “Fuck you, Sammy. That pie was perfect and he had to go and ruin it just because Balthazar sided with me a few times in a row. But the joke’s on  _ him _ because I just dumped the pie on the ground, breaking the crust’s devil’s trap and I ate it like that.”

“Dean. You ate that pie off the floor?” Sam asks in disbelief.

“You bet your sweet ass I did. And every single bite was worth it.”

Sam slowly shakes his head as a figure suddenly appears beside their table. “Hello, boys.”

“Crowley,” they say in unison.

"Dean. Time to get your ass sobered up and back to work. Your next charge turns 18 tonight at midnight.”

“Already?” Dean whines. 

Crowley gives him a sneer before snapping his fingers. Dean’s head suddenly clears of all the effects of the beer he’s been drinking. No more buzz, no more happy floating, just unadulterated here and now. 

“Dude! You couldn’t let me enjoy my buzz while I have to talk to Mr. Stick-up-his-ass?”

“You wish you were sticking something else up his ass,” Sam murmurs under his breath. 

“Alright. Enough children. Come along, Dean.”

Dean stands up, tossing his empty beer bottle and chuckling as it bounces off the side of his brother’s head. “Catch ya later, Sammy.”

With another snap from Crowley’s fingers, the room morphs into HQ. They walk in step towards the elevator. Dean waves at the receptionist who gives him a grin that makes his insides cold. Dean may be a demon, but Eve never stops giving him the creeps. 

Dean lets out a breath of relief once the elevator doors close. He punches in the fifth floor and turns to look at Crowley once the elevator lurches upward.

“Still not a fan of Miss Eve?” Crowley asks with a look of humor on his face.

“She’s creepy, Crowley. I don’t even know why Lucifer keeps her around other than the fact that they’re having gross and kinky sex on the weekends.”

“You sound jealous. You wish you could be having gross hate sex, too?”

Dean huffs, internally cringing at Crowley’s choice of words. He can’t even hear the words ‘hate sex’ without pain in the core of his chest. Dean walks out of the elevator and towards his destination without waiting for Crowley. He braces outside the door labeled ‘Destiel’, taking a deep breath, he pushes his way inside. 

 

**_Seven Assignments Ago, Codename: The Age of Mr. Fizzles_ **

 

Garth stares into the glass case, trying to imagine which ring would look best on Bess’ finger. He’s never felt this way before, and he knows without a doubt that she’s the one.

“You really sure about that, buddy?” asks a voice from his left shoulder.

“Dean, don’t start this again,” comes an exhausted voice from his right shoulder. 

“Howdy, fellas. Glad you could be here to help me choose which ring you think Bess’ll like best.” Garth can’t hide the excitement he feels in his belly. He just hopes he’ll be able to pick the ring that will let Bess know just how special she truly is to him.

“Buddy,” Dean says from the left. “We talked about this. You should be out there playing the field. Spreading your wild oats. You have your whole life ahead of you and you wanna be  _ monogamous?” _

“What’s so wrong with knowing you’ve found the one for you and wanting to be faithful to that one person? Just because  _ you _ could never understand love doesn’t mean you should shame other people when they find it.” 

Garth rolls his eyes. These two never seem to stop fighting. “I don’t think that’s fair, Castiel. I think Dean is more than capable of finding true love just like the rest of us,” he says with his brightest smile. He’s always loved seeing the good in people and Dean’s no different, even if he is the demon on his shoulder.

“See,  _ Ass _ tiel. Garth totally sees  _ my _ point. So go take your perfectly messy hair and shove it.” 

By this point they’ve migrated from his shoulders down to the counter in front of him, still in their mini sizes.

“That I will  _ not _ agree with, Dean. I don’t have a single desire to be with anyone but my sweet Bess. She’s perfect for me and I don’t wanna spend another day without her knowing that.”

“What I’m hearing,” Cas says, as he gets into Dean’s face. “Is that you’re agreeing with me on proposing to our beautiful and perfect Bess. Is that right, Garth?”

Dean’s face turns an unnatural shade of red as he stares Cas down.

“Does everything have to be a competition between you two?” Garth asks.

“Yes!” they shout in unison.

“Are you gonna stop fighting long enough to help me pick out the perfect ring?”

“No,” comes their unison answer.

Garth just shrugs and looks back down at the ring display. He shakes his head as those two continue to fight. Thankfully this one is mild compared to others he’s witnessed. Maybe next time they fight he’ll bring out Mr. Fizzles to help them with their discussion. 

With his mind made up, Garth continues his search for the perfect ring for Bess.

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

Dean sends a silent prayer to any god willing to listen that his hands would calm the fuck down and stop shaking. This isn’t their first rodeo together but somehow they always end up in some sort of screaming match. This time Dean wants things to be different. Especially considering how their last assignment ended... Dean stops that train of thought right freaking there! There’s no way Dean’s reliving  _ that _ memory! Slowly opening the door and walking through, Dean holds his breath. 

“Hello, Dean.” 

The familiar voice does things to Dean that he’d rather not think about at the moment. He looks over the room to find Castiel reading a book, not even acknowledging Dean, other than the time old greeting. The room they’re in is the same every time they get a new assignment. Plain white walls surround them with a few couches and chairs for relaxing. There’s a small mini fridge in the corner filled with some of their favorite things. Plain, simple, but perfect for what this room is meant for.

“Heya, Cas. Fancy meeting you here.” Dean tries for humor but it comes out strangled. 

Castiel merely raises his brow in question without taking his eyes away from the book. Dean decides to just sit down on the couch and wait for their time. The clock on the wall reads 11:50pm so Dean won’t have to suffer with awkward silence for very long. 

Dean’s eyes wander back to the angel and notices what he’s reading. A giant smile breaks out on Dean’s face. “Dude! You’re finally reading Slaughterhouse Five! That’s awesome.”

Castiel’s blue eyes finally leave the page and meet Dean’s. “You’ve talked about it enough I thought I would see what all your fuss is about.”

There’s a warm stirring going on in Dean’s belly. “It’s my favorite. I can’t help raving over it,” he says with a shrug.

Castiel’s lips lift the tiniest bit at the corner. “I like it.” And then he’s back to having his nose buried in the book.

Dean does NOT analyze this exchange. Nope. Not at all. Except his belly is filled with little, stupid butterflies. Dean rolls his eyes at himself and leans back on the couch, the picture of relaxation. 

“Did Crowley give you any information about our next assignment?” Castiel asks, bringing Dean out of his own thoughts. 

“Nah. He likes it to be a surprise. Organic reactions or something like that.”

Castiel gives him a hum for a response. Thankfully the clock dings and it’s showtime. 

A humming starts up in the air until a door, across from the door that Dean came in through, appears. 

“Shall we?” Dean asks, gesturing at the door. 

Cas nods before getting up and walking towards it without waiting for Dean.

“Great. It’s gonna be like that, huh?” Dean murmurs under his breath. 

They both walk through the door. It’s always the same. Bright, white light dimming until they’re inside the bedroom of their next assignment. Dean feels the familiar tingling of his true form showing like it does every time they introduce themselves. He flicks his tail out, feeling it stretch and move after he’s left it hidden for so long. 

“Hello,” Castiel greets beside him before Dean even fully has his bearings. 

Dean looks over to looks at Cas’ wings. They’re always beautiful and breathtaking; Dean will never get used to seeing them in all their glory. 

Finally, Dean looks around the room to see who their charge will be. Sitting on the bed, wiggling with excitement is a cute, little redheaded girl. 

With a wave of his hand, Castiel transports them over to where they belong, on the girl’s shoulders. 

“Hello,” Cas greets. “My name is Castiel and I am the angel on your shoulder.”

Dean rolls his eyes at the formal way Cas always talks to new charges. “And I’m the demon on your shoulder. The name’s Dean.”

Looking back and forth between them, the girl’s grin grows. “Oh. My. God. This is so much more awesome than I ever dreamed it would be! My name’s Charlie, it’s such a huge pleasure to finally meet you.”

“Same here, kid,” Dean says with an easy smile. “So do you have any questions right away?”

“I think I’m pretty well prepared. Everyone already knows you get your shoulder soldiers when you turn 18 and you guys are gonna help me with all my big life decisions. You,” she says, pointing to Dean. “and I are gonna raise hell together. And you,” she points to Cas. “Are gonna help keep me on the right track.”

“It’s a tad more complicated than that, but for now I see you have enough of a basic understanding.”

Dean rolls his eyes again. Could this guy get any more clinical?

“Dean. Could we not start out this assignment acting like children?” Cas huffs. 

Dean gives Cas a salute. “Sure thing, Cas.” Then he turns back to Charlie. “I’m not sure if they taught you this but you’re required to provide us with somewhere private to stay.”

Charlie jumps up from her bed in excitement. “Yes! Of course! I have the perfect thing for you! I think you’re gonna love it!” 

With a snap of his fingers, Dean moves himself from Charlie’s shoulder to her bed. Charlie rummages through her closet and pulls something big out.

“Here you guys go. I hope you like it. I had it made specifically with you two in mind.”

Dean looks closer and he can’t stop the laugh that escapes. “Charlie. This is amazing. No one has ever done something like this for us.”

“This is much appreciated, Charlie.” Cas says as he flies himself down to the floor with his wings. 

“Show off,” Dean whispers. By the glare Cas sends him, Dean assumes it wasn’t quiet enough. 

“I had it made with soundproof walls so it will honestly be your home without worry.” The look of pride on Charlie’s face absolutely melts Dean. He tries hard not to become attached to his charges, but he can already tell he’s not going to be able to keep his distance this time. 

“Thank you, sweetheart.”

Dean snaps his finger and teleports himself right in front of the miniature house Charlie had made for them. It’s two stories complete with its own welcome sign on the white front door. 

Dean nudges Cas with his shoulder, “Let’s go check out our new house, Cas.”

Cas gives him a small smile before opening the front door. They both audibly inhale as they walk inside. The entire place is already furnished with custom built, tiny furniture. 

“Wow,” Dean breathes as he continues further through the house. He goes right which leads to the kitchen. The fridge isn’t stocked but that would be tough without powers. Dean begins to make a mental list of all the things he wants to fill it with.

“Our rooms are upstairs,” Cas says as he begins walking towards the stairs. Dean follows. 

“You wanna take right or left?” Dean asks when they make it to the top. The upstairs is divided into two seperate living areas. 

“I’ll take right since I’m always right.” Cas chuckles at his own joke as he walks towards his chosen room.

“Ass,” Dean breathes as he makes his way to the left. 

When he walks through the door, a smile breaks out on his face. There’s a giant king size bed in his bedroom that looks comfy as hell. There’s dressers and a closet and anything else he would need in a bedroom. He walks to the other door in the room and it leads to a giant bathroom complete with a giant tub. Dean knows he’ll get plenty of use out of that! 

Leaning against the door frame of his room he yells, “hey Angel, you wanna try out this big tub with me? We could snuggle up and take a nice hot bath together.”

Castiel’s muffled reply comes quickly. “Not even in your dreams, Demon!”

Dean snickers and walks back into his room. With a snap of his finger the drawers of the dresser are filled with his clothes, his tv and entertainment system is against the wall opposite the bed, and the closet is filled with the rest of his things. Dean jumps onto his bed, lays back, and relaxes. With a content sigh Dean thinks this is going to be so much better than a stupid fucking shoebox.

 

**_Six Assignments Ago, Codename: The Playboy_ **

 

Castiel watches as Balthazar grabs another drink from a passing waiter. 

“Isn’t this party just wonderful, my little darlings?” Balthazar purs in his usual, posh British accent as he sips from his glass. 

“Hmmm, I don’t know, darling. Seems a bit drab,” Dean responds in his mock British voice. 

Balthar huffs. “You’re drinking free wine and helping me troll for my next belt notch. What could possibly be more exciting than this?”

“Watching the Titanic, singing Celion Dion karaoke, getting my horns removed, a root canal--” 

“Alright, enough.” Balthazar cuts Dean off before he can name anymore ridiculous things. Castiel can’t help but smile at their immature interactions.

“Fine, fine, fine. Let’s get back to the real reason we’re here,” Dean says from his place on Balthazar’s other shoulder. 

“I agree with Dean for once,” Castiel adds. “You said you wanted to get a few business connections to help your law firm. This is the perfect opportunity. There are three gentleman right over there,” Cas says as he points them out, “that would do greatly to help your networking.”

Dean and Balthazar both stare at Castiel before looking at each other and bursting out laughing. 

“You’re so adorable when you’re being all  _ straight and narrow _ , Cassie.”

Dean looks at him fondly, “isn’t he though? Just the cutest little angel,” he says in a mock baby voice. 

Castiel huffs and crosses his arms over his chest. No, he is not pouting.

“Awe, now he’s adorable because he’s being all pouty,” Dean says with a smile. 

“Oh. That’s quite the catch, don’t you think Dean?” Balthazar asks, nodding towards a tall brunette woman at the bar. 

“Hmm,” Dean hums. “I don’t know, Zar. If they don’t pass the Cas standard are they really worth it?”

Balthazar gives a belly laugh. “Fuck! I completely forgot we came up with that system. No sleeping with anyone who isn’t at least as hot as Cassie!”

“Exactly. And Cas is WAY hotter than that chick.”

Castiel’s belly fills with the most confusing sensation as Dean discusses in depth why Cas is more attractive than that woman. He can feel his cheeks warm. He’s flattered. 

“Alright, alright,” Balthazar whispers. “I get it. She doesn’t come close to the Cas standard.” He turns in a slow circle trying to find someone else. His eyes stop on a handsome man. 

“Which one are you staring at?” Dean asks.

Balthazar gestures. “That one. He’s so fucking hot. He’s so hot I’d even let him top.”

Dean lets out a long whistle. “You never bottom, dude. Which one are you talking about?”

“The bear. Wearing the blue suit.”

“That one?” Dean asks in surprise. “We literally just discussed this, Zar. That guy’s nowhere near as hot as Cas.”

“I don’t know, Dean. That guy’s pretty hot,” Castiel murmurs because he does have eyes and yes, that man is very attractive.

“Pff, you’re both blind if you think that guy even holds a candle to Cas,” Dean defends, crossing his arms across his chest.

That warm feeling inside Castiel’s belly intensifies as Dean continues to argue the merits of Castiel’s attractiveness. It’s nice to feel wanted. 

“Dean. I’m going for it,” Balthazar decides before striding towards his target. 

Dean poofs over to sit beside Castiel. He knocks their shoulders together causing Castiel’s stomach to flip in excitement. 

“Don’t worry, buddy,” Dean whispers. “This guy’s a snail compared to you.”

That warm feeling is just him appreciating Dean’s show of friendship. It’s just the warmth of not fighting for once in their work. It has to be the happiness of finally getting along. At least, that’s what Castiel keeps telling himself. 

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

“Castiel!” Dean hollers from the living room. When the angel walks in, Dean points at the board he’s standing in front of. “What the hell is this?”

A wicked smile shows up on Cas’ face. “That would be a scoreboard.”

“Yeah, I got that much. What the hell’s it for and why’s it in our living room?”

Castiel walks up to the board and picks up the dry erase marker that’s sitting on top of it. He writes a giant one under his name and a giant zero under Dean’s. “It’s just me keeping score of this current assignment,” he says with a shrug.

“Seriously, dude?” Dean groans. “The last time we tried to keep track like this you turned into a giant piss baby. You are the worst loser ever!”

"Last time, I was not angry that you won, Dean. I was angry that you kept track of the score in order to flaunt your winnings in my face. You literally ordered a mariachi band to follow me around for an entire day in celebration.”

Dean chuckles. “Those were some good times, Cas.”

“So this time,  _ I _ will be the one to win and then throw it in  _ your _ face in obnoxious, over the top ways,” Cas declares with a smirk.

Dean pats Cas on the shoulder. “Well I think that is a goal and dream that you should think about to help keep yourself inspired. Good for you, buddy,” he says in the most patronizing voice he can manage. 

“Ouch!” Dean yelps as Cas steps on his tail.

“Oops. I’m so clumsy. Didn’t see you there,” Cas says as he walks towards the kitchen. 

Dean stalks after him, only to stop dead in his tracks as the inner pulling begins. Their charge is in need. Dean points and glares at the angel. “This is not over.”

“Wouldn’t dream of it,” Cas snarks back before waving his hand.

Within a blink of an eye they’re once again on their perches on Charlie’s shoulders. Dean looks around their surroundings and is surprised to see they’re sitting in a coffee shop. He looks down, noticing Charlie is working on her laptop while periodically glancing up at the cashier. 

“He’s cute, isn’t he?” Dean murmurs to Charlie who startles.

“Cheese on a cracker! Stop sneaking up on me like that!” 

“Sorry. Kinda comes with the job,” Dean says with a huff of amusement. 

Castiel hops off of Charlie’s shoulder and picks up a piece of paper that Dean hadn’t noticed. “How long have you been contemplating this?”

Charlie’s face turns red as she snatches the paper away. “A while?”

“My vote is that you go for it. The barista is a total hottie, and he’s got a killer smile.”

Castiel snorts. “Of course you’d vote for that.”

“What was that angel? You wish that someone would think of  _ you _ as a hottie with a killer smile?”

Cas taps his chin before replying, “I think your vote is gonna get me another point.”

Charlie butts in, “you are both very distracting. Between the fighting and the wings and the frickin’ tail.” She shakes her head. “I don’t know. I’m sorta shy when it comes to this sorta stuff.”

Dean snaps his fingers causing his tail and horns to no longer be visible. “There’s one thing down. Now onto more pressing matters,” he pauses for dramatic effect. “Ask the cute boy out, Charlie.”

“Wait, are you gay, Dean?” Charlie asks in sudden surprise.

“Nah. Angel over there is gay as they come,” Dean says pointing to Cas. “But I’m bisexual. I play for both teams.”

Castiel clears his throat. Dean glares at him, noticing his wings are gone and pushes down the tiny flicker of disappointment at no longer being able to see them. “Would you care to hear my vote, Charlie?”

“Of course, Cas. Let’s hear you’re big plan, because I’m almost positive it’s leaps and bounds better than Dean’s.”

“Rude,” Dean says under his breath.

“I think you should wait until the lovely lady behind the counter comes out to bus the table across from you. Then you’ll be able to start up a conversation and you can give her your number.” Cas finishes with a look of absolute beaming pride. Dean kinda wants to flick it right off of his pretty face.

“Fuck,” Dean hisses. “I didn’t realize that option was even on the freakin’ table!”

Castiel just gives him a smirk and a shrug. Bastard.

“I like Castiel’s idea,” Charlie says with a head nod like she’s trying to convince herself. “That’s what I’m gonna go with. Shoot, she’s coming now. You guys buzz off and I’ll fill in the deets later tonight.” Right before they leave Charlie looks over at Dean. “And for the record, I’m also as gay as they come.” 

Dean snaps his fingers and they’re back at home. Before Dean can say anything snarky, Castiel walks into the living room. While keeping his eyes trained on Dean, he erases the giant one under his name and replaces it with a two. Then he gives Dean a giant smile before breezing out of the room and up the stairs. 

 

**_Two Assignments Ago, Codename: Break-ups from Hell_ **

 

Dean slowly pours the holy oil from the weird ass jug it came in. He walks as slowly and quietly as he can handle, as he makes a perfect circle around the sleeping angel. Once the circle is complete he takes a step back to admire his handy work. Castiel looks incredibly peaceful as he sleeps, his face relaxed and slack without its usual tension winkles present. A small smile forms on Dean’s face. He attempts to push down all the mushy feelings that are swelling in his chest as he stares. 

Suddenly, the pull of a guardian is stirring in his chest. He waits until the moment Castiel’s eyes open before dropping the lighter onto the oil. The flames catch instantly. Dean watches as Castiel’s eyes widen in surprise. When those baby blues reach Dean they darken in fury.

“Are you kidding me right now, Dean?”

Dean gives a shrug. “This time I guess I’ll be the one to help with the decision.”

“Are you truly this petty?”

“You bet your deliciously sweet ass I am! You keep making these little comments about how inept you think I am. Well guess what buddy, who’s inept now?”

With that, Dean snaps his fingers, finding himself on Ruby’s shoulder. Except the situation is nothing like he thought it would be. Instead he’s dealing with Ruby sobbing.  _ Fuck. _

“Ruby, what’s wrong?” Dean asks as gently as possible.

“That asshole you convinced me to go out with cheated on me,” she hisses at Dean accusingly. “This never would have happened if I would have listened to Castiel but  _ no _ ,’ she says mockingly. “I just had to pick the path that would be more  _ fun _ and  _ carefree. _ ”

Shit. Dean did not think this plan through at all. “I’m really sorry that happened to you, Ruby.”

Ruby scoffs. “Yeah, right. All you care about is me picking your side over Castiel’s!” 

Almost like her saying his name made him appear, the angel pops up on her other shoulder glaring daggers at Dean. 

Dean awkwardly chuckles, “howdy, Cas. Nice of you to join us?”

Castiel ignores Dean in favor of looking at their charge. “Was it that asshole boyfriend, Ruby?”

She gently nods her head. “Yep. He cheated on me. And I’m blaming Dean.”

“Good choice.”

“Hey!” Dean tries to object but is met with matching death glares. “Fine! I know when I’m not needed or welcomed,” he huffs.

Dean teleports himself to the room next to Ruby’s where they’re staying, giving a half assed smile at the burnt ruins of Cas’ bed where he used the mattress to put out the holy oil fire. Unfortunately, his demon hearing is so good he overhears Ruby and Castiel talk about all of the dumbass men in their lives. And Dean’s name seems to be popping up a lot more than he’d like. 

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

Charlie knocks on the tiny door of the playhouse, stepping back she waits for someone to answer. The door slowly opens and her little demon friend pops his head out. 

"What’s up, Charlie?” Dean asks.

“Are you busy? I was wondering if you’d like to watch some Game of Thrones with me.”

Dean gives her a perplexed look. “You wanna hang out? With  _ me _ ?”

She shrugs. “Totally. You’re one of my guardians. It’s only fair we get to know each other better. Come on, dude! It’ll be fun!”

“Alright,” he says tentatively, before snapping his fingers and becoming normal size. Now she’s looking up at him instead of down. 

Charlie leads him to the living room where everything is already all set up. The show is already in and ready to play, popcorn is popped, and there’s an open beer for Dean. 

“Huh. You really wanted to spend time with me,” Dean muses to himself.

“Yep!” Charlie enthusiastically adds. “I really, really did.”

“You’re kinda weird,” he states with a fond smile. “I like it.”

They sit down on the couch and start watching the show. They’re both pretty engrossed but make off hand comments back and forth. It’s comfortable in a way that Charlie loves. She can really see herself becoming best friends with the demon. 

“So what’s the deal with you and Cas?” Charlie asks between episodes.

“Ugh,” Dean grunts before downing the rest of his beer. “I don’t even know anymore.”

“What do you mean?”

“We started off as enemies right off the bat. I don’t even know why we were so angry at each other to be honest. Ever since our first assignment we’ve been at each other’s throats until gradually we just weren’t anymore.”

Charlie tilts her head. “You’re not making a whole lot of sense, Dean.”

Dean shrugs. “We used to hate each other until we gradually just hated each other less and less. But for some reason we still fight. Maybe if Castiel was less of an asshole towards demons we’d be friends. Or even…” he trails off.

“Or even what?” she asks quietly.

“It doesn’t matter,” Dean says with a shake of his head. “It’s never gonna happen. He hates demons. Plus he fucked up too badly. I don’t think I can forgive him.”

“What’s stopping you from going out there and finding someone else then?”

Dean chuckles to himself and glances at Charlie. “I haven’t gotten laid in,” he taps his chin in thought. “Five assignments ago. The stupid fucking heart wants what the stupid fucking heart wants I guess.”

They both sit in silence for a moment before Charlie whispers, “what did he do that was so unforgivable?”

Dean gives her a sad smile. “Last assignment he broke my heart.”

 

**_One Assignment Ago, Codename: Mistakes were made_ **

 

“Cassie!” Gabriel yells as Castiel walks through the door. He takes a moment to look around.

“You’re charge is doing very well for themselves,” Castiel murmurs to his brother.

“That he is! The guy is a genius and he really likes me and Kali so we get free reign of the house.” 

Castiel walks into the house further and sits down at the table. He stares down at his hands. He’s never this nervous, his hands are sweaty and shaking so bad he decides to sit on them. 

“What’s going on, Cassie?”

“I seem to have a problem,” Castiel mumbles.

Gabriel sits down across from him, gaze unwavering. “O-kay? Care to elaborate?”

“Yes.”

Gabriel huffs. “Care to elaborate  _ today _ ?”

Castiel buries his face in his hands. “How do I get over these feelings for Dean?”

“Cassie, that’s so easy! I have the perfect solution for you because I had to deal with the same thing with Kali. She drove me fucking nuts. We bashed heads so often is gave me a headache. Then one day she pinned me to the counter while we were fighting. It was so hot I couldn’t  _ not _ reach out and kiss her. Kissing lead to very, very heated hate sex. Now we occasionally fuck like bunnies and everything is right in the world. No more crazy arguments, no more pent up feelings, no more confusion.”

Castiel finally looks up at his brother who’s leaning back in his chair, legs stretched out in front of him. He looks like he doesn’t have a care in the world. “And this will take these feelings away?” Castiel asks, touching his chest. “All of these confusing, infuriating feelings?”

“For sure, brosky. One or two hate fucks and you’ll be cured on your demon affliction.”

Castiel takes a deep breath, looking up at the ceiling he asks, “why do I feel like this is a terrible idea?”

Gabriel snorts. “Probably because of the giant stick in your ass.”

The ache in Castiel’s chest flares up at those words. The same words Dean uses to mock him frequently with. Why must the demon be so insufferable and yet make Castiel’s stomach flip with butterflies?

“Thank you for your time,” Castiel deadpans. Right before he can snap his fingers and fly back home Gabriel stops him.

“You have to time this just right, Cassie,” he tells his brother seriously. “When things get overly heated and you feel like smiting that demon.  _ That _ is when you reel him in for a kiss. Not a second sooner.”

“I’ll take your words into consideration,” Castiel says before leaving without another word.

Castiel stands in the ‘kitchen’ of their current living situation which happens to be a treehouse. Dean’s back is to Cas as the demon finishes putting some food together. When he turns around, the smile on Dean’s face makes those butterflies flap faster. Castiel’s answering smile isn’t forced.

“Hey, Cas. I’m glad you’re back. I just finished making some peanut butter and jelly sandwiches.”

_ Shoot. _ Those are Castiel’s favorite snack. His face feels like it’s on fire as he steps towards Dean. This gorgeous demon who makes Castiel angrier than he’s ever been in his life, who frustrates Castiel beyond belief, but also gives Castiel glimpses of his kind heart. These little things are making the angel slowly fall in love with a demon. That thought pulls Castiel short. That’s not what this feeling is. Is it?

He stands right in front of Dean. Before he can think better of it he grabs the back of Dean’s neck and kisses him. Dean lets out a gasp of surprise which Castiel uses to his advantage, plunging his tongue into Dean’s mouth. They both moan as their tongues touch for the first time. 

Dean’s mouth tastes like peanut butter and jelly, and Castiel can’t get enough of it. He dominates the demon’s mouth, taking possession of the demon. Castiel pulls back only far enough to begin running his mouth along Dean’s jaw. One of his hands tightens in Dean’s hair, tilting his head slightly to give himself better access. 

“Fuck, Cas,” Dean moans as Castiel bites down on Dean’s neck. Dean shifts his hips forward causing Castiel to gasp as he feels the hard line of Dean’s erection against his hip. It’s incredibly hot and makes Castiel that much more sure of wanting this. He wants Dean.

Gabriel’s warning words scream in his head but Castiel ignores them in favor of memorizing the little sounds Dean makes.

Dean’s hands snake up from Castiel’s hip, lifting his shirt up as he goes. As soon as his shirt is out of the way, Castiel’s lips are back to attacking Dean’s. 

“I’ve wanted this for so long,” Dean pants out between kisses. 

Castiel tenses for less than a second before resuming the kiss. He has to remind himself that this is just a hate fuck. This isn’t real. Dean doesn’t have  _ feelings _ for Castiel, other than the feeling in his pants. It’s no secret that Dean finds him attractive and has wanted to sleep with Castiel since they met. As long as Castiel can remember that Dean is just a demon who likes sleeping around, than  _ maybe _ his heart won’t be  _ too _ broken when this is all said and done.

Dean grips Castiel by the back of his thighs and lifts him up in the air. Castiel wraps his legs around Dean’s waist and throws his arms around his shoulders. When he looks at Dean, he’s assaulted with the biggest smiles he’s ever seen on Dean’s face. 

“Come on, Angel,” Dean whispers as he pecks Castiel’s lips. “I think we should take this to the bedroom.”

That warmth is back in Castiel’s chest as he listens to Dean whisper in his ear. That damn pet name never ceases to make Castiel’s insides turn to goo. He nods enthusiastically to Dean’s question. 

“Take me to bed.”

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

“So, which movie should I take Dorothy to go see tonight?” Charlie asks as she bites her thumbnail. 

“Well, stop that first of all,” Castiel says as he drags her hand away from her mouth, which is no easy thing considering he’s tiny at the moment.

She pulls her hand away but starts nibbling on her bottom lip instead.

“Take a deep breath, Charles,” Dean says. Castiel doesn’t understand the nickname but Dean’s had weirder nicknames for their charges in the past so he ignores it. “You’re both going to have a great time. Just relax.”

Charlie nods her head, letting out a long exhale. “Alright. I’m okay. So which movie do you think would be best?”

“That new Star Wars movie for sure,” Dean answers without any hesitation.

“That would be an excellent geek check,” Charlie says, bobbing her head up and down.

“I think you should take her to that new romance movie that just came out. You can share popcorn and hold hands. It will be romantic,” Cas argues.

“Alright,” Dean says seriously as he stares at Charlie. “I have three reasons why you should pick my idea.” He holds up his first finger. “One, look at that guy with his halo and wings. He’s so lame.”

Castiel raises his eyebrow at the demon. “Really? You’re going with appearances?”

“Not to mention the flasher coat,” Dean says with a snicker before lifted two fingers in the air. “Number two. That guy wants to lead you down the path of  _ righteousness _ ,” he says in a mock sing-songy voice. “I want to lead you down the path that  _ rocks _ !”

When Dean doesn’t continue Charlie asks, “and your third reason?”

Dean jumps off of her shoulder onto the dresser right in front of her. “I can do this!” Dean declares before jumping onto his hands in a perfect handstand. Then he lifts one of his hands to the side. “Ha!”

“What does that have to do with anything?”

“No, no. He has a point,” Castiel deadpans.

“You’re an idiot,” Charlie says before flicking Dean. He flies through the air before slamming into her mirror with a loud thump. “But I begrudgingly like your idea better, Dean. Sorry, Cas. But any girl I’m dating has to like Star Wars.”

“No hard feelings. I just want you to be happy, Charlie.”

Charlie gives him a bright smile. “Thanks, Cas. I want you to be happy, too.”

Castiel tilts his head in question at the odd statement. He’s never had a charge say something like that before. 

“Will you stay with me while I walk to the theater, Cas? I was just hoping we could chat so I don’t have time to think and freak out.”

“Absolutely. I am here for you,” he says honestly.

He sits down on her shoulder as he begins walking at the door, wishing Dean a good night and to ‘not wait up’. 

“So,” she starts. “What’s up with you and Dean?”

And if that wasn’t a loaded question. “I’m not sure what you mean?” he answers, pretending to be oblivious. 

Charlie lets out a huff. “I think you know exactly what I’m asking, dude. You guys sometimes fight like you hate each other’s guts. But then the next minute you’re making googly eyes at each other.”

“I’m not sure what ‘googly eyes’ are but I’m quite sure I’m  _ not _ making them.” Castiel folds his arms across his chest. 

“Yeah, sure. Whatever you say. I’ll believe that when I stop seeing it.”

“It’s complicated,” he tries to explain.

“Well that’s obvious. Maybe you guys should just try fucking already,” she jokes.

“Tried that. Did not help,” he whispers. Apparently not soft enough because Charlie stops walking.

“WHAT?” She yells.

When she turns her head and looks at him, he manages a shrug.

“Oh my god! What happened? Give me some details here!”

“It was a huge mistake. I thought I could get rid of all these feelings I had by having sex with Dean, but everything backfired. He thought we were getting together and I just wanted to fuck the feelings away, as my brother so elegantly puts it.” Castiel finishes talking and looks anywhere but back at Charlie. He knows he screwed up royally and there’s nothing he can do to redeem himself.

“Oh, Cas,” Charlie gently whispers. “You gorgeous idiot. How could you do that to Dean?”

Cas shrugs again. “I didn’t think he cared for me. I assumed my feelings were one sided. I screwed up and I don’t think Dean will ever see me the same way again.” Castiel’s heart breaks a little more every time he thinks about that night. 

Charlie begins walking again, remaining silent. Right before she gets to the theater she stops again. “I don’t think that all hope is lost, Cas. You fucked up but there’s always hope for a second chance. When you get that chance though,” she pauses and levels Cas with a stern look. “Don’t fuck it up again.”

“I will take your advice to heart.”

“Good,” she lifts her fist for a fist bump which Castiel returns with his small hand. “And if I have  _ any _ say in the matter, you guys will get your happily ever after.” She sets Castiel on the ground. Right before walking away she adds, “even if it’s the last thing I do.”

 

**_Four Assignments Ago, Codename: Redheaded Psycho_ **

 

Dean pours a large glass of whiskey and slides it over the table to Cas who nods as he lifts it up to his lips. 

“We should just each drink it straight from the bottle. You know it takes a large amount of alcohol for an angel to get drunk,” Castiel says with a sigh.

Dean nods as he slides the entire bottle over. “You’re right. Just drink it from the bottle.” Dean snaps his fingers, wrapping his hand around the new bottle of whisky that’s appeared. 

Dean stares as Castiel picks up his own bottle and takes several deep swallows from it. The motion of his throat moving, combined with the sight of his lips wrapped around the mouth of the bottle has Dean squirming in his seat. 

“I’ve never felt so helpless during a job before,” Cas murmurs as he stares down at the table. He looks so lost. It makes Dean’s chest ache in sympathy. He’s never seen Castiel so down before.

“If it’s any consolation, I feel the same.” Dean takes a swig from his own bottle before continuing. “I mean, I understand you’re supposed to be upset since she’s choosing the opposite of the good and holy path, but even I hate what she’s doing and I’m a freakin’ demon. I’m programmed to lead people astray yet I wish she’d have listened to you.”

Cas shakes his head. “I knew something was off when she started insisting everyone call her Abaddon instead of Josie.”

Dean huffs. “Yeah. I figured it was a phase, not a freaking cult.” He stares at the wall while sipping his whiskey.

Castiel finally looks up from the table and meets Dean’s eyes. “Thank you for trying to sway her away from what she’s doing. You technically could have been happy she was going down this path but you tried to show her reason.”

For some reason, Cas’ praise makes Dean’s belly fill with warmth. “No problem, dude. I may be a demon but even I know what she’s doing ain’t right. I draw the line at innocent lives.”

They both sit in silence, drinking from their bottles. Castiel finishes his first and when he stands he stumbles a bit. Dean stands and catches him before Cas can fall. They stand chest to chest. Dean realizes his hands are braced on Cas’ chest and he slowly moves his hands back down to his sides as his face flames red. 

“I just wish there was something we could do to stop it,” Cas whispers, eyes never leaving Dean’s.

“I wish we could too but you know the rules. We’re only influencers. We can’t interfere.”

“That rule is so stupid, Dean. I hate it,” Cas’ voice breaks at the end of his declaration. 

Dean’s heart begins to race at being this close to Castiel without screaming in his face. They’re both drunk and swaying. Dean places on his hands on Cas’ shoulder to give him a reassuring squeeze. The contact seems to snap something in Cas because the angel leans forward and plasters his lips to Dean’s.

The surprise causes Dean to freeze in place. Castiel pulls away just as fast as he leant forward, and he stumbles back.

"Shit. This was a terrible idea,” Cas mumbles as he continues to slowly walk backwards. “Why did you suggest we drink, Dean?”

“Dude, don’t blame that on me. Learn to hold your liquor better.”

“I hold my liquor just fine, thank you. Maybe you shouldn’t pretend to care about my feelings while we’re drinking,  _ demon _ ! I swear you enjoy messing with me.”

Dean shakes his head in disbelief. “Seriously, Cas? That’s what you’re gonna go with?” Dean’s stomach turns to lead.

Castiel turns his back, walking towards the door. “I’m not playing your mind games, Dean. I gotta go cool off. Don’t wait up.”

Dean stares in shock as the angel walks out the door without another word. They’ve always fought, it’s in the nature of being opposing influencers but this was something else. Finally being on the same side of an argument, Dean realized maybe he doesn’t hate the angel. Just maybe they could even be considered friends. Hope fills his chest. Friends who kiss when drunk? Dean’s not sure of the logistics, but he can definitely see them at least as friends. Well, looks like there’ll be fat chance of that happening.

Dean finishes his bottle wondering what the hell kind of mind games they’re supposedly playing. Before he can worry too much about anything more Cas related, Dean passes out. 

  
  


**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

A split second is all it takes.

“Trust me, mom. Those two need to just man up and tell each other how they feel. They’re head over heels in love but they’re both too freakin’ stubborn to do anything about it,” Charlie complains.

“You know how men are,” after a pause, her mom adds with a chuckle. “Well, I guess you don’t. Honestly we’re better off without men in our lives. They’re dumb when it comes to their feelings.”

“You can say that again,” Charlie sighs dramatically. 

Charlie’s mom stops at a stop sign and looks over at Charlie. “So tell me more about Dorothy. How did your date go?”

“It was pretty awesome, mom. She’s so beautiful. And she likes Star Wars, which is a huge point in her favor.”

“She sounds great, baby. When do I get to meet her?”

Charlie rolls her eyes. “We’ve only been on one date. Give it some time before we freak her out with meeting the parents shtick.”

“If she’s really good enough for  _ my _ girl then she won’t mind meeting me.” Charlie’s mom states.

Charlie turns in her seat to look at her mom. A snarky reply is right at the tip of her tongue. But then a bright light shines in her eyes. A car. 

Everything happens in the blink of an eye. One minute Charlie’s talking with her mom and the next the car is turned sideways. Her mom is hanging above her, slumped and unconscious in her seat. 

Charlie’s head throbs, there’s something dripping into her eyes that she’s pretty sure is blood, her arms and legs are scratched up from all the glass laying around. 

“Mom?” Charlie asks in a shaky voice. She reaches a hand out to try to shake her mom awake but nothing happens. “Mom!”

Charlie isn’t sure how long she sits in the car, begging her mom to wake up before the paramedics get there. The moment she sees someone come to help, exhaustion takes over and everything slowly blurs then fades to black.

###

When Charlie wakes up again she’s in an ambulance. She jolts awake and frantically looks around. 

“My mom? Where’s my mom?” she cries to the paramedics patching her up. 

“Your mom is in a different ambulance heading to the hospital. I need you to take a few deep breaths, ma’am.”

Charlie’s breathes come out in pants as her mind runs a mile an hour. Everything is wrong. “Is my mom okay? She was passed out in the car! She wasn’t waking up!”

“Shh,” the paramedic coos. “You need to calm down. Your blood pressure is spiking and if you can’t calm down I’m going to have to sedate you.”

Tears stream down Charlie’s face as she attempts to piece everything together. She can feel her heart continue to race and her breathing just won’t calm down. The paramedic is there, plunging a needle into her IV and Charlie surrenders to the darkness.

###

Charlie stands outside her mom’s hospital room. Nothing feels real. The doctors finally sat her down to update her on her mom’s condition. It’s not good. They threw around words like brain dead. She has to choose whether or not to pull the plug. 

Charlie’s hands shake as she stares at her mom. This isn’t fair. She was going to meet Dorothy. It wasn’t supposed to happen like this. 

“Charlie?” comes a soft voice beside her.

When she looks up, her vision blurs from unshed tears. Instantly, two solid bodies encompass her in their arms. Charlie lets the tears fall freely, letting out sob after sob. 

When she’s all cried out, Charlie pulls back and faces her mom again. 

“They want me to pull the plug,” she gets out. Her throat is scratchy from crying and disuse.

“What do you want to do?” Castiel asks.

“I don’t think it’s time yet. I’m not ready to say goodbye.”

“Then don’t,” Dean says. “You do this on your time, sweetheart.”

She nods her head without looking at either of them. 

“Thank you,” she mumbles. “You can go now. My mind’s made up.”

“Are you sure? We can stay here with you, Charlie,” Castiel offers but Charlie shakes her head. 

“I have to do this on my own,” Charlie says. Her angel and demon leave her. She’s going to do  _ this _ on her own. She just has to figure out how to do what she has planned without her little helpers finding out.

 

**_First Assignment, Codename: Pilot_ **

 

The ride up in the elevator is stilted with awkward silence. Castiel is not known for his ‘people skills’ but even he is aware of how awkward this is. The doors open and Castiel exhales in relief.

“Do you have any further questions, Castiel?” Naomi asks as they walk side by side down the hall.

“No, ma’am. I am prepared and ready for my assignment.”

Naomi places a hand on Castiel’s arm to stop him. He turns to face his mentor. “Then let me give you some last minute advice. You’re demon counterpart is one, Dean Winchester. His superior is  _ Crowley.” _ She spits the name out with venom. “Demons are not to be trusted at anytime, Castiel. They are evil, vile creatures.”

Castiel nods along. “I understand.”

Naomi gives him a long look. “I don’t think you do,” she says slowly. “You’ve always been sympathetic but demons are made to be our worst nightmare. It’s in their very makeup. And even worse, you’ve been paired off with Dean. He’s known as a player. He takes great pride and pleasure from making angels fall from their righteous paths. He enjoys corrupting those of us who stand for that which is good and pure. The notches on his belt are beyond counting, Castiel.” She stares right into Castiel’s eyes as she murmurs. “What a disappointment you would become if you too were just another notch on that belt.”

Castiel swallows around the lump in his throat. “Yes, ma’am. I understand. I will not disappoint.”

“Good,” Naomi says as she gestures towards the door labeled ‘Destiel’. “Now off you go. Good luck with your first assignment, Castiel.”

He nods his head. Turning his back to her, he slowly opens the door. Castiel looks around the room. All of his belongings have been moved here previously and he finds a demon glossing through one of his journals.

“Excuse me!” Castiel demands as he stalks towards the demon. “What do you think you’re doing?”

The demon drops the journal back into the box, staring at Castiel like a deer in the headlights. What an unusual act of innocence for someone who is supposedly so evil. 

“Hey, sorry man. I was just trying to get a feel for who I’d be paired with,” the demon says with an awkward chuckle. 

“And you thought the best way to do such was to go through someone else’s things? To snoop?”

“Why don’t we just take a deep breath and calm down a bit,” the demon suggests. “Let’s start over? My name’s Dean Winchester and I’m the demon to your angel.”

“Castiel,” he says in response. 

“It’s nice to meet you, gorgeous,” Dean says while flashing an incredibly handsome smile. All of Castiel’s inner warning signals are shouting at him.

Cas violently takes his hand from Dean’s grip. “Great. They were right about you.” Castiel watches as Dean’s face falls. “Well, for the record I refuse to be another notch on your bedpost. I have more self respect than that!”

Dean’s lips turn into a snarl. “Fuck you, buddy! I have higher standards than some dumbass angel who makes assumptions before getting to know someone first.” Dean flops down in the chair on the other side of the room. “You might be gorgeous but you are a giant bag of dicks.”

Cas storms back over to where Dean is sitting. “I’m a bag of dicks because I have higher standards than you? Well I apologize for not slumping down to your level, demon.”

Dean gives Cas a sickening sweet smile. “Sorry, angel. I didn’t realize I was dealing with someone so incredibly holy. Maybe if you didn’t walk around with that giant stick up your ass you’d have nicer things to say. Especially since your  _ diary _ was telling me about the other things you’ve had up your ass…. Oh wait…”

Castiel stands with his mouth open in shock. “How dare you,” he begins in fury only to be cut off by their duty. The door to their assignment begins to appear. 

“Fuck!” Dean hisses. “I’m so glad to be starting this job in such a great mindset. Can we just try not to be such dicks when it comes to our actual guardian duties?”

Castiel turns his nose up at the demon. “Like you really care,” he murmurs before adding. “I promise to be civil when it comes to our duties. I do not take our job lightly.”

Dean begins walking towards the door. “This job is an honor and I don’t wanna screw it up.”

The small flash of sincerity gives Castiel pause. Maybe demons aren’t fully evil?

Dean gives him a look of irritation, “Are you coming, dickbag?” And Castiel’s distrust is back.

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

The first place Charlie starts her search is the local library. She assumes there must be books on black magic and demon deals somewhere in this dusty old place. She was wrong. After searching through every single room and shelf, she came up empty. These things are apparently not common knowledge, which makes sense. What Charlie is looking for is dark and scary, but she’s determined to find it anyway. 

Next, she tries to figure something out through the grapevine. One of her friends had to have at least  _ heard _ of something like this, right? She ends up coming up with nothing again. 

Feeling frustrated and discouraged, Charlie opens up Craiglist just for shits and giggles. She knows this isn’t the type of place to find what she’s looking for but she tries regardless. 

_ Exactly what you’re looking for… _ is the title to one add that happens to catch Charlie’s eye. What’s the harm is clicking?

_ Are you at the end of your rope with nowhere left to go? Are you desperate enough to consider ANYTHING? Email me and we just might be able to make a deal. _

That’s it. That’s all the add said. Yet, it was enough for Charlie, because she  _ was _ desperate. She  _ was _ at the end of her rope.

She types as quickly as she can asking for more details. She bites on her thumbnail, watching as the email indicator changes from sending to sent. Now comes the hardest part. The waiting.

###

The answer Charlie got was confusing. She had a task to complete before she could meet up and make the deal. 

Which leads to Charlie inviting her guardians to watch a movie with her in the living room. She knows they’re worried about her, but she pushes her feelings down. Charlie’s on a mission and she refuses to let them interfere. She’s not going to let them in on her secret. She has to do this alone.

Time feels like it’s standing still but eventually the movie is over. She wishes the boys a good night with a hug. During said hugs she gets exactly what she needs. A single hair from each of them. 

Once she’s alone again, Charlie sends another email. With that sent, she takes out her other supplies. Laying them one by one inside the little bowl, dropping in the hairs, then saying the Latin words before dropping in a match. The contents glow a light blue. It’s done.

###

Charlie gets out of her car and walks into the bar. She’s never been here before but it’s the meeting place they agreed on. She finds a corner booth and sits down. 

Running her fingers through her hair, Charlie startles when someone slides into the booth across from her.

“Hello, darling,” the red headed woman greets in a cheery Scottish accent. “I take it you completed the spell exactly as I instructed.”

Charlie nods her head. “I did. They won’t be making an appearance tonight.”

The woman claps her hands together once. “Wonderful! Then why don’t we get started?”

“Okay. As you know I’d like my mother saved. She’s braindead right now.”

“Oh sweetie, that won’t be a problem in the slightest. Easy peasy.”

Charlie slowly nods her head. “Right. And in exchange, all you need is my soul?”

“Precisely, little one. I will restore your mum to full health. You’ll have her back exactly how she was before that wretched car accident. In exchange, I’ll be taking your soul.”

“Okay, I’ll do it,” Charlie says, taking a deep, shaky breath.

The red headed woman tilts her head and taps her chin thoughtfully. “Now you’re just a precious wee one still. I’ll throw in a little bonus for you, dearie. I won’t be collecting your soul for one month instead of taking it tonight. You’ll have a blessed month with your mum and be able to get your house in order. Once that month is done and over with, then I’ll come a calling.”

Charlie feels tears well up in her eyes. One month. One month will be worth it. “Thank you,” she whispers.

“Now none of that, sweetie,” the woman says as she gently wipes the tears from Charlie’s cheeks. “Do we have a deal, dearie?”

“We do,” Charlie whispers. 

“Alrighty. Let’s seal this deal with a kiss and call it a night, shall we?”

Charlie plants her hands on the table and leans forward, pressing her lips firmly against the other woman’s lips. 

 

**_First Assignment, Codename: Pilot_ **

 

Dean walks through the door labeled ‘Destiel’ with his superior, Crowley, by his side. 

“So this will be your starting point for each new assignment. Across from you will be the door that shows up when it’s time for you and your partner to go to your charge.”

Dean nods along as he looks around the room. All of his possessions have been transported here along with his partner’s things.

“Any questions before I leave, squirrel?”

“What’s my angel like? Have you met them?”

Crowley sighs as he walks over to a shelf Dean hadn’t noticed before. He pours himself a drink. Staring down at the swirling amber liquid he finally answers. “I know his mentor.  _ Naomi _ ,” he spits the name out. “If he’s anything like her than he’s going to be the most judgemental, holier than thou art, asshole. Angels seem to be all the same. They don’t care about the balance or the reason we’re here. They see our black eyes and assume the worst.”

Dean thinks maybe Crowley went through one too many bad breakups and is taking it out on all of angel kind but there’s no way he’s going to actually say that. “They can’t all be that bad, Crowley.”

Crowley scoffs as he downs his glass. “You’ll find out the hard way soon enough, Dean. They’re all pompous asses who don’t give a damn about anyone but themselves. One wrong move and you’re on their shit list for life. No forgiveness or compassion like they preach.” Pouring himself another glass, Crowley sits down on the couch. “Before I was a mentor I too was a guardian. I was paired with this angel named Gabriel.” Crowley sighs before sipping at his drink. “You would never have guessed which of us was the demon and which was the angel. I was busy always making sure our charge wasn’t doing anything incredibly stupid while Gabriel was busy playing tricks.”

Crowley stands and walks towards Dean, offering him a glass of his own. When Dean shakes his head, Crowley continues his story. “We had this one charge in particular. He wasn’t very bright. Always trying the next big drug that all his friends were trying. One night he thought it would be a good idea to try LSD,” Crowley explains with a scoff. “Bloody idiot. Gabriel decided it would be funny to show the guy ‘his true form’ which was just him changing his appearance to have three heads and wings that were completely covered in eyeballs. Poor bloke had nightmares the rest of his life!” Crowley shakes his head, eyes far off. “And yet I was the  _ evil _ one because I ended up helping one of our other charges get into magic. He was an incredibly gifted warlock who practiced with his twin sister. Max,” Crowley remembers with a twitch of a smile on his lips. The smile is gone almost as quick as it was there. “No matter. They’re all the bloody same. After watching my angel counterpart fuck up time and time again, it only took that one thing to turn him against me.”

“Alright.” Dean says slowly. “I’ll try to keep myself in check to keep things working smoothly. Thanks for the advice, boss.”

Crowley pats Dean’s shoulder on his way out. “Good luck, Dean-o. I have a feeling you’re going to need it.” Well, that’s not ominous at all.

Dean strolls around the room, looking around at everything. He stops in front of an interesting looking box. Browsing through he finds its a box filled with books and one of those books is calling his name. He reaches in, pulling out a beautifully bound journal. 

“Huh,” he murmurs to himself. “What do we have here?”

Dean thumbs through the book. The handwriting is incredibly elegant and Dean can’t find it in himself to look away or put the book back down. The words flow almost gracefully together. 

There’s a page Dean stops at that’s all about a woman hitting on the writer, who repeatedly turns her down because he’s gay.  _ Interesting, _ Dean thinks to himself with a smirk.

Suddenly, the door opens and a storm of righteous fury barrels right for him. Dean drops the journal in shock. Dean’s mouth opens and closes like a fish in his distraction. This guy is breathtakingly beautiful. Too bad his inside isn’t as nice as his outside. As soon as the guy’s mouth opens, Dean’s forced on the defensive. 

The angel is abrasive, judgmental, and insulting. Dean tries to defuse the situation but nothing seems to cool this guy down. By the time the door opens for them to meet their first charge Dean is confused and angry. Dean won’t admit it out loud but he’s also hurt. He’s never been the best at feelings, but he’s determined to fight fire with fire when it comes to this furious beauty known as Castiel.  _ More like Asstiel, _ Dean thinks with a snort.

Dean’s going to be a professional but that doesn’t mean he’s going to be a doormat to some angel who thinks his shit don’t stink. His first priority will be to his charge. His second priority is going to be to knock this guy down a peg or two, and if that happens to be getting his charge to pick his side at every crossroad? Well, that’s just a bonus. 

The angel turns his nose up to Dean. “Like you really care,” he murmurs before adding. “I promise to be civil when it comes to our duties. I do not take our job lightly.”

Dean begins walking towards the door. “This job is an honor and I don’t wanna screw it up.”

Dean waits for a response. When he doesn’t get one he adds with irritation, “are you coming, dickbag?”

Castiel follows behind him with eyes that practically glow with righteous fury.

Fuck that guy for thinking so low of Dean without even taking the time to know him! Fuck that guy for being so gorgeous, even in his anger, that Dean’s pants are uncomfortably tight. But most importantly, fuck Crowley for being right.

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

A dreadful, sinking feeling hits Dean’s gut all at once. Something’s wrong. 

“Dean!” he hears Cas yell, just as he was about to yell for the angel.

They run out of their rooms, meeting in the hallway. 

“Something’s wrong,” Dean says frantically.

Castiel nods his head. They both turn to leave their mini house to try and find Charlie. If they’re both sensing something is wrong, it must be Charlie. Once outside, they both grow to normal size in a flash. 

“I hear people in the living room,” Cas states. 

In the living room, they’re greeted with Charlie’s blinding smile. And Charlie’s mom. The mom who was brain dead just an hour ago and is now walking around with a giant smile on her face preparing them all dinner.  _ Fuck. _ Dean knows this isn’t good. 

“Hi, guys!! I was just about to come knock on your door! My mom is home from the hospital!”

“That’s great, Charlie,” Dean says suspiciously. 

“How did this happen?” Cas asks with a furrowed brow.

“The doctor’s said it was a miracle,” Charlie declares but she can’t look at either of them as she says it, going back to fuss over her mom. Dean and Castiel look at each other.

“Fuck, Cas,” Dean whispers. “How bad are we talking here?”

“I suppose it would depend on which you think is worse. Black magic or a demon deal.”

“Son of a bitch,” Dean murmurs to himself. 

###

Back in the tiny house, Dean’s pacing back and forth in front of Cas, who’s currently sitting on the couch with his head in his hands.

“Fuck!” Dean says again. This has been his primary reaction today. “I don’t know what we can do here.”

“I don’t know if there’s anything we  _ can _ do. We’re under strict rules, Dean.”

“I know that, Cas. I fucking know. It doesn’t make this any easier,” Dean says with anger as he continues to pace. He can’t sit still. His nerves feel fried. He hates feeling this helpless, especially when it comes to someone he genuinely cares about. Why the hell did this girl have to needle herself into their hearts?

“What did you two talk about at your last movie night, Dean?”

Irritation instantly flares up in Dean’s chest. “Don’t try to pin this on me, Cas. You  _ know _ I would never in a million years suggest something like this. Just because you look down at me because I’m a demon doesn’t mean I would want Charlie to sell her fucking soul!”

“I wasn’t implying that,” Cas says with a huff. “I was just hoping for some sort of clue.”

“Well did she say anything to  _ you _ last time you spent time together?”

Castiel looks up from the floor to glare daggers at Dean. “No. She did not.”

“Didn’t think so,” Dean murmurs under his breath as he continues his pacing.

“I still can’t figure out how she even came to a decision without us knowing.”

“That’s it!” Dean declares as his feet plant in place. “That’s our loophole!”

“I don’t understand.”

“She made a decision without us being present. The rules say ‘once a side is chosen, interference is prohibited’.”

Castiel stands up. “A side wasn’t chosen in this decision. Therefore we aren’t breaking any rules in getting involved! Dean, you’re a genius!”

“I’ve been trying to get you to admit that for years, Angel,” Dean says with a grin. He can’t help it, he’s so happy to be able to help!

“Can you not be an assbutt right now?” Cas asks with an exhausted sigh. “Let’s at least  _ try  _ to be serious until after we figure this out.”

Dean’s grin instantly falls. “Fine,  _ Asstiel _ . Let’s be tight laced and get to work.”

Ignoring Dean’s attempt at poking, Castiel states, “first we have to find out how exactly she saved her mom. If it’s black magic there’s not a lot we can do. If it’s a demon deal we’re going to have to try bargaining with the demon that she worked with.”

Dean claps Castiel on the shoulder. “We can do this.” Then pauses before adding, “we might be able to do this. But we have to actually work together.”

“I can put our past behind us if you can,” Cas says with a raised eyebrow, almost in challenge to Dean.

“Clean slate. Let’s figure this out, for Charlie.”

“For Charlie.”

 

**_Five Assignments Ago, Codename: Clarence’s Biggest Fan_ **

 

“Hello, boys,” Meg purs as her guardians pop up on her shoulders. She absolutely loves making decisions now that she has help from these delicious boys.

“Hello, Meg,” the angel greets politely as the demon crosses his arms, glaring. These two are too funny.

Meg gestures towards all the packets scattered across her bed. “I’m trying to decide which house to put an offer on. Hence the summon.”

“Alright, alright. I’ve totally got this,” Dean says as he hops off of Meg’s shoulder and strolls through the different options. “Let’s see,” he ponders as he taps his chin. 

“You better go look through them too, Clarence. I wanna know your opinion as well.” Meg says with a wink.

Dean grumbles something under his breath that she doesn’t catch. It makes Castiel tense.

“Now don’t be getting jealous, Dean,” Meg teases.

“Jealous?” Dean huffs. “Of Mr. Always-Has-His-Panties-In-A-Wad? Not even a little bit.”

“Mmm,” Meg purs. “I’d love to see my sweet Clarence in a pair of panties.”

“Enough you two,” Castiel demands. “Let’s all be civilized and focus on these houses.”

“It’s pretty hard to focus when all I can think about is seeing your magnificent ass in a snug pair of panties, Clarence.”

Dean groans before Castiel replies. “I assure you, you will never be graced with that visual in real life.”

“Right,” Dean snarks while flipping through a new packet. “We wouldn’t want anyone to think Castiel is  _ deviant _ enough to do such a thing.”

Castiel throws down the packet he was looking through. “We can’t all be content to sleep with anything that looks at us. Some of us have standards and prefer healthy, monogamous relationships.”

“Oh, juicy,” Meg whispers to herself as her little friends get even more heated.

“And  _ some  _ of us can’t live like monks. There’s nothing wrong with finding a suitable companion for a night of fun. It’s consensual and everyone leaves very, very happy,” Dean states, adding vigorous eyebrow action for good measure.

Castiel snorts. “It’s nice to know you can live with yourself after sleeping with everyone within a ten mile radius everytime we get a new assignment.  _ I _ on the other hand, couldn’t take it. Sex is intimate and supposed to be special.”

“Well it sucks you can’t find someone so special,” Dean says quietly without looking at Castiel. “Maybe you’d find that person if your head wasn’t so far up your ass,” he finishes with venom. “But instead you’ll just keep bitching about me and how I can’t do a single thing right.”

Castiel pauses for a second before responding. “Maybe if you weren’t such a manwhore you’d be able to see my point of view,” he says with a shrug.

“Fuck you, Cas,” Dean grits between clenched teeth. “You’re such an arrogant dick that you can’t see what’s right in front of you. Happiness could bite you in the ass and you wouldn’t even fucking notice.”

“And you have a suggestion where I can find it?” Castiel asks in a mock sweet tone.

“Yeah. Right here, sweetness,” Meg states, breaking the tension.

Dean and Castiel make small smiles at her before continuing on with their house debate. She picks Dean’s choice again which leads to yet another argument. This time about how Meg can hit on and flirt with Castiel without ever actually picking his side. She just laughs and shrugs. Her silly little helpers.

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

Castiel watches helplessly as time goes by without any leads on how to help his charge.  He can’t go to any of his mentors because they are sticklers for rules, and Castiel doesn’t wish to chance getting him and Dean in trouble. The last time he went to Gabriel for advice, things did not go as planned. He feels absolutely helpless. It’s been about a month since Charlie’s mother woke up and they’re running out of time to find who’s responsible. Soon they’ll be forced to resort to extreme measures and Castiel has a sinking feeling in the pit of his stomach that nothing good will come of that.

“Dude,” Dean greets as he gets back from speaking with Crowley. Castiel didn’t think it was wise for Dean to go see his mentor about this matter, but the smile on his face tells him they might have finally found a lead. 

Dean strolls over to the fridge to retrieve a beer for himself. He leans back against the counter. “Were you able to get anything off of her computer?”

Castiel shakes his head. “I was not. I’m not overly surprised,” he says with a sigh. “She’s a computer programmer. I’m sure she erased all of her steps so we wouldn’t be able to get any information that way.”

“Figures,” Dean says with huff before sipping his beer. “Maybe I should take a crack at it just in case. See if I have any better luck.”

Castiel hackles rise. “You’re such an assbutt sometimes, Dean. If you truly think you can outsmart Charlie’s computer skills, go ahead and try. But if you are only offering because you think  _ I _ couldn’t figure it out then save it.”

Castiel watches as Dean rubs the back of his neck. “You’re right. Fuck. I’m sorry, Cas. I’m just so fucking stressed about everything.” He shakes his head and sips his beer. “We were right by the way. About the loophole. Crowley is a meticulous bastard when it comes to rules and contracts but in this case it worked in our favor and if anyone tries to come after us for interfering he’ll have our backs.”

Castiel feels his shoulders loosen slightly. Finally, something is working out for them. Castiel watches Dean wordlessly as the demon continues to stare at the wall and sip his beer. The worry lines across his eyes and forehead further show how invested Dean is in this mission. All those treacherous feelings come back full force. This demon is beautiful despite all of their ups and downs together, he truly cares. Just maybe--

“Fuck!” Dean yells as he and Castiel both clutch their chests. Tightness and pain radiate around his heart so suddenly it takes his breath away. “What’s happening?” Dean cries as his eyes meet Castiel’s. The green eyes Castiel have slowly come to love look truly panicked and afraid. 

Just as fast as the pain started it ended. Only now there’s an empty feeling left behind. “Oh no,” Castiel whispers. “Oh no. Oh no. Oh no.”

“Shit, Cas. This is bad, man.” Neither of them can feel Charlie’s presence anymore. It’s like they have no charge at all. 

They frantically search through the house but come up short. She’s gone and they have absolutely no way of finding her without that connection. Again, Castiel is left feeling completely and utterly helpless.

###

They sit, side by side on the couch, waiting for Charlie to come back home. Castiel can almost pretend that they’re a united front, together finally, but there’s just too much at stake at the moment to ponder such things. 

Castiel glances over at his demon counterpart, watching as Dean’s brows frown, deep in thought as he stares down at his hands. He’s nervous and anxious just like Castiel. Everything inside the angel is screaming at him to breach those few inches and take Dean’s hands into his own. To offer some sort of comfort to the demon. He’s pulled from his thoughts as the door bangs against the wall with the force with which it’s kicked open. 

“What’s up, bitches,” Charlie calls as she walks into the living room. The moment she lays eyes on Castiel and Dean she stops in her tracks. “Hey, Daddies! Did I miss my curfew or something?” she jokes as she strolls into the room and plops down into one of the armchairs, throwing her feet over one of the arms as she slumps in the seat. 

“Charlie?” Dean tentatively asks, no doubt thinking the same thing as Castiel;  _ this is not their Charlie. _

“Who else would it be? You got any other red headed badasses you’re in charge of?”

“What’s happened to you? You’re not acting like yourself,” Castiel says, pointing out the obvious. 

Charlie scoffs as she turns in the chair the right way. She plants her feet on the ground, folding her hands and resting her chin on them as she looks right at them. “I think we all know what’s happened. I saved my mom. I paid a price to save her,” she says with a shrug. “Doesn’t seem all that high of a price to me.”

“Where are you going?” Dean demands as Charlie gets up from her seat. 

“Thinking about trying out that new gay club that opened up in the next town over. You wanna come with me Dean? We could both go get laid, especially since it’s been, what? A couple hundred  _ years _ since you’ve gotten any.”

“What about Dorothy?” Castiel asks as his heart begins to ache.

Charlie throws her head back and laughs. It’s not her usual laugh and it gives Castiel chills. “I dumped her on my way home. I don’t need anyone holding me back. It’s not like I feel anything for her anyways.”

“Charlie,” Dean starts, his voice breaking. “Who did your deal for you?”

“Some chick named Rowena. Nice accent. Pretty hot for a crossroads demon,” she answers, not even caring enough to hide anything anymore. 

Charlie walks out of the room without further comment, leaving Castiel and Dean to deal with the fallout. 

“Fuck, Cas. She doesn’t even realize how bad this is. We have to do something!”

Finally, Castiel reaches over and touches the demon. Resting his hand on Dean’s shoulder he says, “let’s start with finding Rowena.”

###

Castiel follows Dean into the bar where Rowena is known to be found according to the demon grapevine. The tall, attractive redhead isn’t hard to find in a booth towards the back of the bar. 

“Hello, boys,” she says without looking up for the book she’s reading as they slide into the booth across from her. 

“Rowena?” Castiel asks.

“Aye. What is it that I can do for you?” she asks in her lilting Scottish accent. When she finally looks up her eyes widen and a giant grin forms on her face. “Well, what a handsome pair we have here.”

“We’re here because our charge recently made a deal with you. We’re here to bargain.” Dean stares her right in her eyes, back straight with confidence and Castiel can’t help but admire the demon more and more. 

“Drats. You’ve just missed your opportunity. The soul’s already been passed off to my boss.”

“Who’s your boss?” Castiel demands. They is no way they’re giving up so easily!

“Ah, ah, ah. Information like that does not come cheap. You did say you’re here to bargain,” she says with an even bigger grin then before. 

Castiel rolls his eyes but it’s Dean who speaks for them. “What’s your price?”

Rowena turns her eyes to Dean. “You’re a Winchester, aren’t you?” He nods. “I’d like a date with your moose of a brother.”

“What?!” Dean sputters as his eyes go wide. “Seriously?  _ That’s _ your price?”

“It is, darling.” Her eyes go far away and wistful as she says, “he’s just so big and handsome and that hair. I could go on but I’m sure you have a phone call to make.”

Castiel watches as Dean huffs but immediately pulls his phone out of his pocket.

“Sammy! Yeah, I have the biggest favor to ask you and I can’t let you say no.” Dean runs his fingers through his hair. “No, it’s not something stupid like last time.” After a pause, “no! That was a one time thing, man. You can not hold that against me!” 

Castiel watches with fascination as Dean begins to blush. “Remember that one time. No that that time! The other time! Yeah, with the panties and the dancing.” Dean’s face floods bright red. “Exactly. Poughkeepsie, Sammy.” Dean nods slowly, a small smile forming on his lips. “Yeah. It’s really  _ that _ important. And it’s only one date.” Dean looks over at Cas with a wink. “Perfect. Thanks, Sammy.”

Finally, Dean looks at Rowena with fire in his eye, “now, about your boss.”

###

“Dean,” Castiel says as he keeps his eyes moving, looking for any signs of danger through the trees as they stand at the edge of the forest, a beautiful lake to their backs. “I don’t think this is our best plan.”

“Listen to the angel, demon-boy! This is a lost cause. Just let those hellhounds take me. My time’s up and there’s nothing you can do to stop it,” says the older gentleman sitting on the dock, fishing like nothing out of the ordinary is going on. 

“We’re not here to stop them, dumbass,” Dean grumbles. Then he turns his attention back to Castiel. “This is gonna work, buddy. Dick Roman holds Charlie’s soul. He might be a tough ass but he’s a sentimental bastard. Once we have one of his hellhounds we can use them as leverage in a trade. Simple.”

“You make it sound so easy.” Castiel paces as he waits, adjusting his glasses that allow him to see the hellhounds. “Just be careful. Hellhounds will attack anything that threatens them and I’d rather leave here in one piece.” He doesn’t add that he’d like to leave without worrying about Dean as well. The demon can hold his own. At least that’s the reassurance the angel continues to tell himself.

Dean shrugs and adds, “what’s the worst that can happen?”

###

Three hours pass as they pace and wait for the hellhounds to show. It took awhile to find someone who sold their soul with a contract that warranted the visit of hellhounds. The grumpy old man continues to fish as Castiel lines the entrance of the dock with Goofer dust to keep them from getting to their destination. 

The first howl makes them both tense, gripping their weapons tighter. Castiel holds his angel blade in one hand and an enchanted collar in the other. 

“You ready, babe?” Dean breathlessly asks as he gets into a low crouching fighting stance. The endearment slipping out, and Castiel is positive the demon has no idea what it’s doing to Castiel’s insides. “Cause here they come!”

Castiel prepares himself. Thankfully, only one hellhound breaks through the trees. She prowls back and forth, watching the two of them with distrustful eyes. She snaps her jaw, growling at them in displeasure at being delayed from her demonic version of fetch. 

Ever so slowly, Dean shuffles further to Castiel’s right, trying to get on the hellhounds’ other side. It spooks the hound enough for her to finally attack. It comes full force, head-on towards the angel, snarling as she goes. Castiel allows the beast to tackle him, maneuvering to avoid it’s bone-crunching bite. Drool drips down the beast’s fangs onto Cas’ face as he struggles to hold her jaw away from him. She snaps only inches from Cas’ cheek as the angel grunts under her weight.

Dean, taking the advantage of catching the hellhound from behind, snaps the collar around its neck. 

“Sit!” he commands and the hellhound obeys, watching Dean with distrust.  Dean stares at the hellhound until it submits and lays down. Then those beautiful green eyes look over at Castiel. A wide smile breaks across Dean’s face as he slowly begins to laugh. It’s beautifully carefree and Castiel can’t look away.

“We did it! We actually did it!”

“Don’t sound so surprised. It was your plan after all,” Castiel says, unable to stop the giant grin on his own face. He wipes the hellhound’s drool from his face, eyes never leaving Dean’s smiling face.

“I know, but that doesn’t mean I wasn’t worried. Fuck,” he breathes as he runs his hand over his face. “So many things could have gone wrong. And when she jumped on you like that? Dude, my heart stopped for a second.”

Castiel tilts his head. “I don’t understand.”

Dean rolls his eyes. “Really? You’re gonna make me spell it out?” When Castiel has no answer Dean continues. “You’re an idiot. But you’re  _ my _ idiot! And the thought of losing you---”

Dean’s cut off by a ferocious growl and suddenly he’s on the ground. The coppery smell of blood overtakes Castiel’s senses as his brain catches up to the picture in front of him. A second hellhound. On top of Dean. Ripping his side open. Biting his shoulder. 

“Dean!” Castiel cries as his body moves without his consent. The hellhound is so distracted with its prey that it never sees Castiel coming. He barely stops himself from plunging his blade into the beast and instead collars it. “Off!” he yells with so much righteous fury that the hound tucks its tail and backs away. 

“Fuck,” Castiel gasps as he looks down at Dean. He’s covered in blood and the gash on his side continues to spew blood. “No, no, no, no, no! This isn’t happening.”

Dean’s eyes are closed and his breathing is ragged and stilted. He coughs, causing blood to bubble from his mouth. Everything suddenly becomes laser focused in Castiel’s mind. All the doubts and questions and insecurities and denials are gone. Everything is crystal clear. His feelings are real. And now it might not matter. 

“No! Dean! I’m supposed to have more time. This isn’t how things are supposed to happen!” Castiel pleads, trying to hold down against the open wounds to stop their bleeding. The blood keeps pouring between his fingers and Cas admits defeat. Instead he holds the demon tightly in his arms, not caring that his clothes are becoming drenched in blood. He holds Dean’s face between his hands, looking at his face which is becoming more and more pale. His glasses fog as his eyes begin to water. “Dean! Listen to me! Listen to my voice! I’m your idiot! I’m yours! I’m so sorry I couldn’t say it sooner!” 

All of these lifetimes together and it take something like this to make Castiel understand. All the snarky comments, all the fights, all the supposed hatred were all just smoke screens and mirrors, attempts at hiding his own feelings from himself. This demon who knows exactly how to push Castiel’s buttons is also the one who has the most gentle heart, always takes care of their charges, who genuinely cares for Castiel. And Castiel missed it.

“Dean, don’t die,” his voice breaks. “Don’t you fucking dare! Because I love you!” Castiel’s tears slide down his cheeks and land against Dean’s face. “I love you. I love you. I love you!” He grips the demon’s shoulder in a panicked grip so tight it makes Castiel’s hand feel hot. Castiel leans down, placing a frantic kiss against Dean’s lips, wishing with everything inside him that this won’t be their last kiss. “Please, Dean,” Castiel whispers.

 

**_One Assignment Ago, Codename: Mistakes were made_ **

 

Dean can’t believe any of this is happening. One second he’s putting together a sandwich for Cas and the next minute he’s got the angel in his arms. Dean’s entire body feels like it’s on fire. He’s never been this filled with need before in his existence. Castiel, angel of the Lord, is kissing him. 

“Fuck,” Dean mumbles as he walks towards his bed. “This feels like I’m dreaming. Is this real?”

Cas bites down on Dean’s neck hard enough to leave a mark. “That feel real enough for you?”

Dean groans. He never would have known Cas could feel this way about him. Dean always assumed his feelings would always be unrequited but right now, Castiel is kissing him so hard and with so much passion it makes Dean’s head spin. 

Dean drops Castiel down onto the bed and quickly crawls on top of him. Kissing his way down from Castiel’s neck to his nipples, reveling in the little noises that Cas makes as he goes. Dean gives each hard nub attention with his tongue and teeth until Cas is squirming under him. 

“Dean,” Castiel moans and it’s absolutely music to Dean’s ears. His cock is aching in his jeans, wanting more.

Dean relieves himself of his own shirt and then flips them over so Castiel is straddling his lap. 

“Let me see your wings,” Dean breathes as he runs his hands over the angel’s hard stomach. 

Castiel gives him a questioning look before shrugging and releasing his wings. Dean audibly gasps as they unfold from behind Cas’ back. They’re beautiful and Dean can’t wait to bury his fingers in them. 

Dean reaches up, grabbing Castiel by the neck, he pulls him down into another sloppy kiss. Cas behings to grind his ass against Dean’s hard cock causing Dean to moan into Cas’ mouth. The friction is maddening. “Fuck,” Dean whispers as they break apart. 

“I love your wings,” Dean murmurs as he gently reaches up to touch. They’re soft and everything Dean’s ever hoped they would be. As he runs his fingers through, Castiel tilts his head towards the ceiling and moans, low and rough. Dean’s dick twitches in response. 

“Cas, you’re so fucking beautiful.”

Castiel’s face snaps down to look at Dean with hard eyes. “Stop making this harder than it has to be, Dean.”

Dean’s hand instantly drop back down to his sides. He looks up at Cas in confusion. “What do you mean?”

“We both know what this is. Stop trying to make it confusing.”

Dean sits up so Castiel is sitting on his lap, chest to chest. “What the hell is that supposed to mean, Cas?” Dean gently places his hand on the back of Castiel’s neck, gently carding his fingers through the soft hair there. “I’m not doing anything confusing. I’m trying to make love to you.”

Castiel sharply turns his face away from Dean. Dean’s heart drops to his stomach and his belly fills with dread. He read this all wrong. 

“You can’t be serious right now,” Cas scoffs. “Don’t pretend, Dean.”

“I’m not pretending anything, Cas.”

Castiel’s eyes begin to water and Dean’s fingers itch to wipe them away. “This is just a hate fuck,” Cas declares. “This is me trying to fuck the feelings away. So come on,” he says, grinding his ass back down on Dean’s now very uninterested dick. “Let’s get this over with so we can go back to just being two people who work together. We can go back to hating each other without all these feelings and all this tension.”

Dean manhandles Castiel off of his lap, standing up, he turns back and looks at Cas. “I thought you were the angel in this relationship.” Dean’s eyes sting with unshed tears as he stares at the angel he thought was finally returning his feelings. “Fuck you, Cas, you son of a bitch.”

Dean quickly throws his shirt back on. “Don’t be like this, Dean.”

“You’re such an idiot, Cas. If you truly thought either one of us could just ‘fuck our feelings away’ without either of us getting hurt then you are far dumber than you look.” Dean turns his back and begins to leave the room. Right before leaving he turns back, “I guess you’ll just have to learn to live with the fact that you just screwed both of us over by doing this. We could have had something great. Something explosive but you’re too scared of your own feelings.” Dean shakes his head as he stares at the ground. “I love you, you dumbass. But good luck getting me to forgive you for this,” he whispers as he teleports away. 

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

Castiel gently removes the glasses from Dean’s face before throwing his own in the dirt as well. He leans down, kissing Dean one last time before burying his face in Dean’s neck. Castiel begins to openly sob into Dean’s shirt collar, not caring one bit about anything else. His whole body feels paralyzed with deep, deep sorrow, he’s sure he’ll forever be stuck right here in this moment. He feels Dean’s breathing stutter and slow as his tears continue to fall. Castiel feels helpless.

“Dean, no,” he rasps against the demon’s neck. “It’s not fair. I love you.”

Suddenly, the chest against his cheek lets out a low groan of pain. It’s more reaction than Castiel ever dreamed of hearing. He lifts his head in disbelief as he watches Dean’s eyes begin to flutter and then open, staring right into Castiel’s eyes. Castiel leans back enough to look over Dean’s body and finds his side is no longer bleeding and the giant bite on his shoulder is slowly patching itself up. 

“What?” he begins saying but a gentle hand on his cheek stops him. His eyes snap back to Dean’s face as the demon stares, a slow, gentle smile forming on his lips. 

“You love me?” Dean asks so quietly Castiel almost doesn’t hear it. 

“I do. I love you, Dean.” The smile that breaks out on Dean’s face takes Castiel’s breath away. It’s the most beautiful thing he’s ever laid eyes on and it feels like he must be dreaming because there’s no way this is actually happening. He must have passed out while watching Dean lay in his own blood. That thought is gone as soon as Dean’s strong grip pulls him down by the back of his neck. Castiel kisses him without hesitation.

When they pull apart, Dean’s face glowing with joy. “Oh my god!” the demon yells right in Castiel’s face, startling him. “You’re a fucking disney princess!”

“I don’t understand,” Castiel murmurs which only makes Dean’s smile bigger. 

“You healed me with a kiss, you big ol sap.” Dean explains. “Your grace must have mojoed my body back together. You kissed your prince charming, causing him to wake from his slumber.”

Castiel can’t stop himself from gripping Dean’s shoulders in a death grip as he buries his nose back in Dean’s neck. “I can’t believe you’re alive. I’m so happy, Dean,” his voice breaking at the end of his declaration. He’s so overcome with emotions and all he truly wishes to do is feel just how alive Dean is. 

“If you two are done sucking face and bleeding all over my fucking lawn, why don’t you get the hell out of here!” the old man on the dock yells, causing both of them to startle. “And take those fucking mutts with you!”

Castiel looks up at Dean and finds the demon trying to hold back his laughter. “You’re welcome, asshole!” Dean yells before Castiel waves his hands and teleports them away. 

They land in Castiel’s bedroom, back in their dollhouse. Castiel feels wild and he knows his eyes must reflect that. He needs to feel that this is real, that Dean is truly alive. “Dean,” Castiel whispers against Dean’s lips. “I need-” his voice cracking before he can even try to articulate what he needs. Thankfully, Dean seems to understand.

Dean quickly works on unbuttoning Castiel’s shirt as their lips forcibly meet once more. Castiel’s hands shake as they grip tightly against Dean’s hips. Too much adrenaline from coming so close to losing this, so close to never experiencing this. 

“Shh,” Dean whispers, trying to calm the angel down. “Calm down a bit, Cas. It’s okay.”

Castiel takes a step back. “It’s  _ not _ okay. I held you in my arms while you were  _ dying _ , Dean.” Castiel’s sight begins to get fuzzy with unshed tears. “Look at our shirts!” he demands. “That’s your blood! We almost didn’t get this because I was such a fucking idiot!”

“Hey,” Dean coos as he takes Castiel into his arms, stopping him from yelling any further. “You’re  _ my _ fucking idiot,” Dean whispers against Castiel’s ear and the angel swears he can feel Dean’s smile. “We’re here  _ now _ . Nothing else matters because we understand each other now, right? This isn’t some stupid one time thing?”

Castiel shakes his head. “No. I’m sorry, Dean. This is real. I love you!” Castiel says with such emotion, praying Dean can tell how truthful he’s being. 

Dean smiles before kissing Castiel again. It starts off slow, their lips barely touching. Dean’s hands finish unbuttoning Castiel’s shirt before pushing it off of his shoulders. Then he lifts his undershirt and brings it over Castiel’s head. They break apart long enough to remove Castiel’s shirt before going back to kissing, this time tilting their heads and deepening the kiss. 

“Wait,” Dean says breathlessly as he pulls back. “Where’s the hellhounds?”

Castiel smirks, “in your room.”

Dean nods his head before pulling Castiel back into the kiss. This time there’s more passion, more tongue, more teeth. Castiel’s hands find their way to the hem of Dean’s shirt to pull it over his head. 

“Please, Dean. Please! I just. I need,” Castiel’s hands are shaking again and his entire body feels like it’s vibrating with bone deep need. 

“Okay. I’ve got you, baby.” Dean pulls back and strips the both of them quickly from their clothes. Then he crowds Castiel back until the back of his knees hit the bed. They fall down with Dean on top of him. The weight of the demon is perfect, grounding Castiel into the moment. 

Castiel grinds his hips up, causing their erections to slide against each other. The feeling forces a wild cry to leave his throat without his consent. Dean grinds down harder and Castiel’s body lights up with pleasure. The demon begins trailing kisses down Castiel’s jaw and neck, occasionally biting down and leaving marks in his wake. On one particularly perfect placed bite, Castiel reaches up and grips Dean’s shoulder. The contact immediately makes them both tense with uncontrollable need.

Dean’s dilated, lust filled eyes meet Castiel’s. “What the fuck is that?” Dean moans. 

Castiel gently pries is hand away, letting out a shocked gasp as his eyes meet Dean’s shoulder where a perfect replica of his hand is raised on Dean’s skin, almost like a burn or scar. Possessiveness rises up in Castiel’s chest as his cock twitches in pleasure. 

“Mine,” Castiel grits through clenched teeth as he grips the hand print again. He can feel their mixed precome dribbling down onto his belly as their need for each other spikes higher and higher. 

“Fuck, Cas. Need you  _ now!” _

“Yes,” Castiel cries. “Need to feel you, Dean. Need to know you’re really here. Need to know you’re alive and with me!” Castiel waves his hand, prepping his channel in one motion. 

Dean snaps his fingers, his cock instantly covered with lube, before pulling himself off of Castiel’s lap. He manovers himself between the angel’s thighs, pulling them up towards his chest exposing Castiel’s prepped hole. “Ready, gorgeous?” Dean asks in a husky tone.

“Please, Dean. Do it!” Castiel’s fingers grip the bed sheet below him so tightly that his knuckles turn white. Dean slowly pushes forward just hard enough for his cock head to slip into Castiel’s hole. Castiel clenches in an attempt to pull Dean in further but one look into Dean’s beautiful green eyes has Castiel relaxing, allowing the demon the control.  Dean continues to thrust forward, agonizingly slow, until he’s completely buried inside Castiel’s ass. “Oh my,” Castiel whispers as Dean brings himself down so he can kiss Castiel’s lips.

“Cas,” Dean murmurs as he pulls back, looking into Castiel’s eyes. “I can barely believe this is really happening.”

Castiel sniffles as he tries to reign in his emotions. Dean is alive. Dean is here. Dean  _ loves _ him. It feels like he’s about to come loose at the seams. His visions blurs and he doesn’t try to stop the tears from falling. Everything inside the angel is  _ longing _ for Dean, wanting to get impossibly closer. Castiel doesn’t understand, they are literally as close as they can possibly be, in the most intimate way. Yet, his grace is singing for the demon. 

Dean begins to gently thrust, inching his hips back until only the head of his cock is inside Castiel before smoothly sliding back in to the hilt. Castiel’s eyes widen and his mouth drops open in disbelief as he realizes what he’s feeling hits him full force. 

"Dean! I’m inside you!”

Dean looks down at him with a huff of amusement, “actually, I’m the one inside you.”

“No,” Castiel rolls his eyes. He grips the handprint on Dean’s shoulder, closing his eyes as he feels  _ his _ grace inside of Dean, bring them even closer on a new and wilder level. 

“Oh shit,” Dean curses as begins moving inside Castiel again, this time harder like he just can’t stop himself. With his hand planted on Dean’s shoulder, every sensation between them becomes magnified. “Your grace saved me.  _ You _ saved me.”

“I’d do it again. Even if I had to give you every single ounce of my grace, I’d do it!” 

Dean’s hips pick up speed, drilling into Castiel’s ass. The sounds of their heavy breathing and the slap of skin against skin fill the room. Dean grips Castiel’s hips, pulling Cas’ ass onto his lap to get a better angle. He begins to peg Castiel’s prostate on every thrust. 

“Fuck, Cas. I love you,” Dean’s voice mingles with moans of pleasure. “Not gonna last very long. Not with you gripping my shoulder with your sexy mojo!”

Dean lets out a growl as he begins to come inside of Castiel. The angel can feel every pulse and every warm drop twitch inside him. It’s heaven. But the best part is feeling the grace inside of Dean react. It’s like a million fireworks all going off perfectly at once, breathtakingly stunning and all together overwhelming as it drags Castiel over the edge right along with the demon. His semen coating both of their bellies as his body radiates pleasure. 

They lay, curled together on the bed, breathing each other’s air. Dean gives him a tiny, intimate smile before pulling out and rearranging them on their sides, facing each other. Gentle touches are shared over their sweaty skin.

“We could have been doing this for so long,” Castiel bemoans. 

The fondness he sees in Dean’s eyes makes his chest tight, not knowing if he truly deserves it. “We have lifetimes and lifetimes to make up for all of that lost time, Cas.”

Castiel’s face breaks out into a giant, gummy smiles as he leans forward, connecting their lips again. They kiss softly, getting lost in the sensations of being together.

Unfortunately, real life calls. They break apart as they hear loud whining coming from Dean’s room. 

“Shall we finish this mission?” Castiel asks with an amused huff.

Dean smirks, “absolutely. The sooner we get Charlie’s soul back, the sooner I can get you naked again.”

 

**_Three Assignments Ago, Codename: Advanced Placement_ **

 

Castiel sits at the foot of the bed looking at his charge. Kevin Tran has every reason in the world to be happy. He’s successful and rich, his career is outstanding with being the youngest neurosurgeon in the country, and he’s well respected in his profession. Yet, here he is, crying in his bed, while eating a tub of ice cream. 

“Let’s talk this through, buddy,” Dean says as he passes Kevin another tissue, who uses it to haphazardly wipe his face and nose before going back to his ice cream.

“What’s there to talk about? I’m pathetic.”

“You are  _ not _ pathetic, Kevin!” Dean starts. “You are an amazing person. Do you need us to list all the things that make you amazing?”

When Kevin continues to stare into his ice cream like it has every answer in the world Castiel picks up where Dean left off. “Well Kevin, just for starters you’re only 26 and you already have a well established career. You’re the youngest in your field which is extremely impressive, especially when you account the amount of schooling you went through just to get to where you are.”

Dean clasps Kevin’s shoulder. “Dude, literally just this morning you saved someone’s life by removing a tumor. You’re like a real life superhero!”

Kevin shakes his head. “I wouldn’t expect you guys to understand.”

“You play the cello better than anyone else I know,” Castiel blurts out.

Dean gives him a weird look before adding, “random but very true. You could have played professionally if you’d felt like it. But you choose the tough path of medicine. You’re making a difference with your work and even with the medical papers you write.”

“Doesn’t change the fact that I’m the kid of the hospital. My coworkers hate me because they think that I think that I’m better than them.” Kevin takes a giant bite of ice cream before adding in a muffled voice, “I mean yeah, I am better than them but that doesn’t mean I’m a jerk about it like some people.”

Dean shakes his head. “You just have to let them get to know you.”

“That’s part of why I’m so pathetic! Don’t you see?” Kevin says, his voice getting frantic. “I am the biggest loser. I have all these accomplishments under my belt but I have absolutely no one to share them with but you. And my mom. How sad is that?” Kevin’s head falls back against his headboard. “I’m 26 years old and I’m still a virgin. I mean damn, I haven’t even been on a date before. I’m lonely and I doubt you can truly relate to that.”

Castiel is stunned into silence. His heart picks up as he thinks about his own situation. Always being with his charge and his co-guardian but always feeling like he’s on the outside. Never feeling like he truly fits in. And yet at the same time he’s always conflicted with these overwhelming feelings towards Dean. He sees glimpses of the demon that make his heart swoon and his stomach fill with warmth. If only--

“You’re not alone, Kevin,” Dean softly says as he looks down at his hands. “I understand where you’re coming from. Sometimes...Sometimes I wish I could go back and do things over. And, I don’t know, I mean there’s…. There’s things,” Dean clears his throat and finally looks up. Those beautiful green eyes lock with Castiel’s. Cas only sees vulnerability and sincerity in them. “There’s people, feelings I want to experience differently than I have before. Or maybe for the first time.” 

Castiel can’t take his eyes away from Dean but the demon looks away and looks anywhere but back at him. Dean clears his throat, patting Kevin’s shoulder in reassurance.

“You life isn’t over, dude. You’ve got so much time left to change things if you’re not happy. I think you should think about accepting the next invite one of your coworkers gives you. They’re always meeting at that bar across the street on Thursdays after work. Go. Make those connections with people.”

“I don’t know if I can, Dean.” Kevin says as he stares at the demon helplessly.

“We will help you. That’s what we’re here for, Kevin. Maybe you could trying bringing in some of those brownies that your mother makes. I’m sure everyone would love those. It would be a nice ‘ice breaker’.” Castiel adds, using finger quotes. 

Kevin finally smiles. “You really think it’s not too late?”

Dean stares into Castiel’s eyes before saying with conviction, “it’s never too late to change things.”

 

**_Current Assignment, Codename: It’s Charlie, Bitches_ **

 

Dean steels himself for what’s to come. He needs to make himself appear to be as demonic as possible, even though the angel next to him makes his insides feel like goo. Looking over to give Cas one more smile, he squeezes the angel’s hand before allowing his face to go blank, putting up walls to hide his emotions. 

Dean opens the door of Dick Roman’s conference room. The man looks up from his laptop, giving them both a giant smile that give Dean the creeps.

“Hello, gentleman. I hear you have something of mine?”

“We do,” Dean says casually. “And we’ll happily give them back.” Dick opens his mouth to reply but Dean quickly cuts him off, “for a trade.”

Dick’s smile never leaves his face as he leans back in his chair. “And what is it that you boys would like from me?”

Castiel is the one to answer beside him. “We’d like Charlie Bradbury’s soul. Once you void her contract and return her soul we will gladly hand over both of your hellhounds.”

“Hmm,” Dick hums as he stands from his chair. He moves over to look out the window, turning his back to Dean and Cas. “What makes you think I even care about those nasty mutts? Bianca and Casanova are quite replaceable, not nearly worth the cost of a soul.”

Dean smiles as Dick turns to them with a questioning eyebrow. “And that’s where you’re wrong. Someone who doesn’t truly care for their hellhounds doesn’t give them special names, Dick. And Casanova? Really?”

“Dean,” Cas chastises. “Not the point.”

“Right. The point is this, we both have something the other wants. Let’s make it a fair trade, it’s just business.”

Dick’s smile returns in all its creepy glory. “Alright, boys. You make a hard bargain that I just can’t refuse.” He walks over to them, sticking out his hand he says, “we have a deal.”

###

Dean feels like he’s on top of the world, literally nothing can stop him. He’s got Charlie’s soul hanging around his neck and he’s got Castiel by his side. Just thinking about what they did today brings up all of those overwhelmingly amazing feelings again that make his heart pitter patter, his stomach sumersault, and his dick thicken. He glances over at  _ his _ angel and smiles. He’s still honestly trying to wrap his mind around the fact that Cas loves him and he can have a repeat performance whenever he wants, it’s almost unbelievable.

“You’re not sleeping, Dean,” Cas chuckles when he notices Dean pinching himself, again. 

“Just making sure,” he says as he bumps his shoulder with Cas. 

“Trust me, I’m as overwhelmingly happy as you are.” Cas reaches down to intertwine their fingers together, squeezing them hard. “This is real.”

The smile that Cas gives him will mostly likely take his breath away until he literally draws his last breath. God, he’s becoming such a fucking sap…

“Besides,” Cas says with a flirtatious wink, “you love me.”

“Well of course I do!” Dean says as he opens the front door of Charlie’s house, leading them in. “You’re my very own Disney Princess!”

They both giggle like two high school kids with their first crush. They’re broken from their little bubble by a sharp gasp, “what the fuck!”

They both look up to see Charlie standing before them. In the little time they were gone she’s cut her hair real short and started wearing dark eyeliner. Her hands cover her mouth as she stares at their intertwined hands. 

“What,” she whispers, her eyes turning glassy. “I should care.”

“What?” Castiel prompts because right now she’s not making a whole lot of sense.

She points at their hands. “I should care about that. I should care that somehow you both got your head out of your asses and talked about your feelings,” her voice beginning to become louder and agitated. “I should  _ care!  _ But I don’t! I don’t feel a goddamn thing!”

“Oh, Charlie,” Dean whispers as he lets go of Cas’ hand and takes a step towards her.

“I should care and I can’t because I don’t have my soul. Oh my god, what have I done?”

Dean grabs her and she sinks into the embrace, burying her face against his chest whispering “why don’t I care? I should care” over and over again. Castiel comes behind her and together they engulf her in their arms. 

“Do you really wish to care again, Charlie?” Castiel asks after gently kissing the back of her hair.

“Yes!” she cries. “Yes! I wanna care! I wanna feel again!”

Dean takes the necklace off holding Charlie’s soul inside. It swirls around the glass like it’s searching for its owner, yearning to be connected with Charlie again. 

“Bottoms up, sweetheart,” Dean whispers as he gently places the vial into her hand. 

Charlie’s hand shakes as he looks at the vial. She looks at Castiel and then at Dean for reassurance. She pulls the top off before quickly throwing the vial back like a shot. 

Dean waits, holding his breath, as Charlie’s eyes close. Dean’s not sure how long they all stand there, waiting for something, for anything. 

“Ho-Ly. Shit!” Charlie yells when she opens her eyes. “I go darkside for like two days and you two get together? Are you fucking serious right now?”

Dean lets out a watery laugh as he pulls Charlie into a borderline painfully tight hug. “You scared the shit outta us, Charlie.”

Dean lets go only to have Cas grab hold of Charlie in an equally bone breaking hug. “We’re so glad you’re okay.”

“Alright, alright,” she murmurs, pushing them both away. “Now spill! I wanna know every single detail!”

“A piece of me is inside Dean,” Castiel blurts out before his face goes bright red. Dean can’t help but laugh. 

Charlie on the other hand gives him a look that the cross between disgust and curious. “What? No. Don’t tell me.  _ Those _ types of detail I don’t wanna hear!”

“But Charlie!” Dean whines. 

“Nope. Don’t even start, Winchester!”

“Fine,” Dean says with a huff. “Alright. Let me tell you the story of how my own personal angel became my very own Disney Princess,” he says, giving Cas a fond smile even though the angel just rolls his eyes at him.

“OMG! Please tell me he gave you true love’s kiss!” Charlie squeals as they make their way to sit down in the living room.

Dean grabs onto Cas’ hand, giving it a small squeeze. He smiles and says, “yeah, something like that.”

 

**_One Assignment PC(Post Charlie), Codename: I Like Nougat_ **

 

Dean loves moments like these, where he’s awake, looking down at a sleeping angel in his bed. Castiel’s hair is more messy than usual, face relaxed, soft snores escaping. Perfection.

“I can tell you’re staring at me right now,” Cas says in his sleep filled, husky voice that makes Dean wanna jump his bones. 

Dean gingerly flicks Cas’ nose. “You’re just so fucking adorable when you’re sleeping, baby.”

“You said it’s creepy when I do it,” Cas whines which makes Dean chuckle. He gently pets the side of Cas’ face, feeling the stubble there. 

“So fucking beautiful,” Dean murmurs.

Castiel lets out a content sigh. “We should stay like this all day. S’nice.”

“Wish we could, baby, but duty calls!” he calls as he snaps his fingers away. Dean is still cackling as he lands on Jack’s shoulder. 

“Hello, Dean. Where is Castiel?” Jack asks without looking up from his laptop.

“Mr. Halo decided to sleep in, buckaroo, so I guess you’re stuck with me,” Dean says with a giant smile. 

Suddenly, Castiel appears on Jack’s other shoulder, giving Dean a glare so furocious he’d be dead if looks could kill. 

“Hello, Castiel. I’m glad you could join us. Dean said you wanted to sleep in today.”

“Trust me, Jack. I would choose coming to see you over seeing that  _ demon _ anyday,” Cas says through gritted teeth. 

“Don’t be like that, baby,” Dean says, raising his hands in surrender. 

“Don’t call me that, Dean!”

“Do you guys always fight like this?” Jack asks so innocently.

“Yes,” they say in unison. 

Dean’s face breaks out into a smile as he whispers, “don’t let him fool you, Jack. This is our favorite brand of foreplay.”

Castiel and Jack’s faces both go bright red and Dean does an inner dance of victory. 

“Not the time, Dean,” Cas says with a stern look.

Dean throws his head back in defeat. “Fine,” he says in the most childish way he can manage. “What’s on your mind, Jack?”

Jack sputters, face turning red again as he looks pointedly at his laptop. “Jack? It’s okay to tell us. We’re only here to help you,” Cas says gently.

Jack nods his head before looking across the library at a boy working on his own laptop. Then he shrugs his shoulders helplessly. “I don’t know,” he says, biting his lips. “I have a crush on someone and I don’t know what I should do about it.”

Dean looks across the library at the boy, who keeps sneaking little glances at Jack. When the demon looks harder, he can see the boy talking to his own guardians, and, oh shit! That’s Sammy and Jo!

“Dude!” Dean says, hoping down onto the desk, gesturing for Cas to join him. “Check it out! That’s Sammy and Jo’s charge over there! We gotta get them together so we can hang out with them more!”

“Dean, we cannot force something like this for the wrong reasons,” Cas says in his best scolding tone.

Dean rolls his eyes. “I wouldn’t do that, Cas. I just watched that boy throw glances over at Jack five times since we got here. Jack’s feelings are obviously returned.”

“Well what do you propose? You’re always ready to jump into things without a plan!” Cas says, folding his hands over his chest. 

Dean turns towards Jack who’s staring at them with wide eyes. “What do you say, Jack? Whose side would you pick today?”

Jack grimaces before timidly asking, “do you still have that bet going?”

Dean grins, winking at Cas, “course we do. Whoever’s side you pick gets to bottom that night. And I’m thinking that Cas’ ass needs a break after you’ve picked his side the last four times! So you should totally pick my side.”

Jack opens his mouth to say something but it quickly snaps shut as his eyes lift. “Umm, hi,” he stutters out. 

Dean looks over to see the guy from across the library standing at their table looking hella nervous.  _ Good, _ Dean thinks,  _ our Jack is worth being nervous over. _ And shit, when did he get so goddamn sentimental?

“I, umm, I got you this,” the boys says as he opens his backpack. He digs something out before placing it on the table in front of Jack. 

Jack’s face breaks into the biggest smile that Dean’s ever seen from the kid. “Thank you, Clark! I like nougat!” 

“I know,” Clark says with a smile of his own. “Umm, I was wondering,” he says as he rubs the back of his neck. Dean watches as Jo flicks Clark’s ear. “Would you like to go to dinner with me?”

“Like a date?” Jack asks, hope written all over his cute little face.

“Yeah, a date.”

“Yes!” Jack blurts out before be calms down and says, “I mean, yes. I would really like that.”

Dean wraps his arm around Cas’ waist as he watches the boys plan when their date will be. He kisses the side of Cas’ head and murmurs, “I love you.”

“Love you, too. And by the way, I’m am definitely counting this as  _ you _ winning,” Cas says with a wink.

Dean bites Cas’ ear, whispering, “I was hoping you’d say that!”


End file.
